37927-29-0

Basic information

• Product Name: (11beta,17alpha)-11,17-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid
• Synonyms: (11beta,17alpha)-11,17-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid;(17R)-11β,17-Dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid;Δ1-Cortienic acid;Androsta-1,4-diene-17-carboxylic acid, 11,17-dihydroxy-3-oxo-, (11beta,17alpha)-;(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-diMethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid;Prednisolone iMpurity B (carboxylic acid);Prednienic Acid;Prednisolone Impurity B
• CAS NO: 37927-29-0
• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.41744
• EINECS: 253-719-9
• Mol File: 37927-29-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 570.7°Cat760mmHg
• Flash Point: 313°C
• Appearance: /
• Density: 1.33
• Vapor Pressure: 2.11E-15mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.78±0.70(Predicted)
• CAS DataBase Reference: (11beta,17alpha)-11,17-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (11beta,17alpha)-11,17-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid(37927-29-0)
• EPA Substance Registry System: (11beta,17alpha)-11,17-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid(37927-29-0)

Safety Data

• Hazardous Substances Data: 37927-29-0(Hazardous Substances Data)

Usage

Description

(11beta,17alpha)-11,17-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid, also known as Prednienic Acid, is a glucocorticoid steroid derived from the androstane class of steroid hormones. It possesses a unique chemical structure with hydroxyl groups at the 11-beta and 17-alpha positions, and a carboxylic acid group at the 17 position. This structure endows it with specific biological activities and makes it a valuable compound for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
Prednienic Acid is used as a key intermediate in the synthesis of various anti-inflammatory compounds. Its unique structure allows for the creation of macrolactonolides by conjugating Prednienic Acid with macrolides, which are known for their potent anti-inflammatory properties. This application is particularly relevant in the development of new drugs to treat conditions such as arthritis, asthma, and other inflammatory diseases.
Used in Drug Synthesis:
Prednienic Acid serves as a versatile building block for the synthesis of a wide range of steroidal drugs. Its chemical properties make it an ideal candidate for the development of new pharmaceuticals with improved efficacy, reduced side effects, and targeted delivery. This application is crucial in the ongoing efforts to discover and create novel therapeutic agents to address unmet medical needs.

InChI:InChI=1/C20H26O5/c1-18-7-5-12(21)9-11(18)3-4-13-14-6-8-20(25,17(23)24)19(14,2)10-15(22)16(13)18/h5,7,9,13-16,22,25H,3-4,6,8,10H2,1-2H3,(H,23,24)/t13-,14-,15-,16+,18-,19-,20-/m0/s1

Synthetic route

prednisolon (50-24-8) → (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0)

Conditions	Yield
With periodic acid In tetrahydrofuran; methanol at 20℃; for 2h;	100%
With sodium periodate; sulfuric acid In methanol; water at 20℃; for 16h; Inert atmosphere;	98.8%
With sodium periodate In methanol; water for 0.5h; Heating; Large scale;	97%

C20H25BrO5 → (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0)

Conditions	Yield
With hydrogenchloride; chromium chloride; mercaptoacetic acid; zinc In ethanol; water at 10 - 30℃; for 0.5h; Temperature; Inert atmosphere;	98%

Loteprednol etabonate (82034-46-6) → (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + 17α-ethoxycarbonyloxy-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Conditions	Yield
With heptakis(2,6-di-O-methyl)cyclomaltoheptaose; water at 37℃; Kinetics; Activation energy; Further Variations:; Temperatures; Reagents; Solvents; Hydrolysis;

11α-hydroxy-androsta-1,4-diene-3,17-dione (898-84-0, 96893-16-2, 7801-18-5) → (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: acetic anhydride; phosphoric acid / dichloromethane / 5 h / 0 - 5 °C / Inert atmosphere 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / 50 - 60 °C / Inert atmosphere 2.2: 1 h / -5 - 5 °C / Inert atmosphere 3.1: sodium hydrogencarbonate; potassium fluoride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 3.2: 5 h / 25 °C / Inert atmosphere 4.1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 5.1: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 6.1: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme

androsta-1,4,9(11)-triene-3,17-dione (15375-21-0) → (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / 50 - 60 °C / Inert atmosphere 1.2: 1 h / -5 - 5 °C / Inert atmosphere 2.1: sodium hydrogencarbonate; potassium fluoride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 2.2: 5 h / 25 °C / Inert atmosphere 3.1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 4.1: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 5.1: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme

C25H38O3Si → (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; potassium fluoride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 5 h / 25 °C / Inert atmosphere 2.1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 3.1: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 4.1: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme

C20H26O3 → (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 2: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 3: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme

chloro-methylsulfanyl-methane (2373-51-5) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → methylthiomethyl 11β,17α-dihydroxy-3-oxo-androst-1,4-diene-17β-carboxylate

Conditions	Yield
With triethylamine	98%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + chloroformic acid ethyl ester (541-41-3) → 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride

Conditions	Yield
With triethylamine In dichloromethane at 0 - 10℃; for 0.5h; Large scale;	96%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane at 20℃; for 3h; Time;	90.2%

dichloroacethyl chloride (79-36-7) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → 17α-dichloroacetoxy-11β-hydroxyandrosta-1,4-diene-3-one-17β-carboxylic acid (199331-37-8)

Conditions	Yield
With sodium hydrogencarbonate In methanol; dichloromethane; water	95%
With sodium hydrogencarbonate In methanol; dichloromethane; water	95%
With sodium hydrogencarbonate In dichloromethane; water
With sodium hydrogencarbonate In dichloromethane; water

dichloroacethyl chloride (79-36-7) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → 17α-dichloroacetoxy-11β-hydroxyandrosta-1,4-diene-3-one-17β-carboxylic acid (199331-37-8)

Conditions	Yield
With potassium hydrogencarbonate In dichloromethane; water for 2h;	93%
With potassium hydrogencarbonate In dichloromethane; water for 2.5h;	93%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → 11β-hydroxy-17-methyl-18-norandrosta-1,4,13(17)-trien-3-one

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane; acetonitrile for 1h; Ambient temperature;	88%

9-deoxo-9a-aza-9a-demethyl-9a-(3-aminopropyl)-9a-homoerythromycin A (92594-46-2) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → C60H101N3O16 (442638-01-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	88%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + diisopropyl-carbodiimide (693-13-0) → (17R)-3'-isopropyl-2'-isopropylimino-11β-hydroxyspiro-3,4'-dione

Conditions	Yield
With copper dichloride In 1,4-dioxane; acetonitrile for 1h; Ambient temperature;	86%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + 2-(4-methoxyphenoxy)ethylamine (50800-92-5) → C29H37NO6

Conditions

Yield

Stage #1: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 2-(4-methoxyphenoxy)ethylamine With triethylamine In N,N-dimethyl-formamide at 60℃; for 1.5h; Inert atmosphere;

75%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + (L)-phenylalanine ethyl ester hydrochloride (3182-93-2) → ethyl 2-(11β,17α-dihydroxy-3-oxo-androst-1,4-dien-17β-carboxamido)-3-phenylpropionate

Conditions	Yield
Stage #1: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 8℃; for 16h; Stage #2: (L)-phenylalanine ethyl ester hydrochloride With triethylamine In N,N-dimethyl-formamide at 0 - 8℃; for 16h;	70%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + diisopropyl-carbodiimide (693-13-0) → (17R)-3'-isopropyl-11β-hydroxyspiro-2',3,4'-trione

Conditions	Yield
With water In N,N-dimethyl-formamide for 7h; Ambient temperature;	66%

di-p-tolylcarbodiimide (726-42-1) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → 11β,17α-dihydroxy-3-oxo-N-p-tolyl-N-(p-tolylaminocarbonyl)androsta-1,4-diene-17-carboxamide

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 80℃; for 1h;	63%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + glycine ethyl ester hydrochloride (5680-79-5) → methyl 2-(11β,17α-dihydroxy-3-oxo-androst-1,4-dien-17β-carboxamido)acetate

Conditions	Yield
Stage #1: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 8℃; for 16h; Stage #2: glycine ethyl ester hydrochloride With triethylamine In N,N-dimethyl-formamide at 0 - 8℃; for 16h;	57%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + methyl [4-(3-aminopropoxy)benzoate] (85873-34-3) → C31H39NO7

Conditions	Yield
Stage #1: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: methyl [4-(3-aminopropoxy)benzoate] In N,N-dimethyl-formamide at 60℃; for 2.5h; Inert atmosphere;	54%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → 6α,11β,17α-trihydroxyandrosta-1,4-dien-3-one-17β-carboxylic acid

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane for 12h; Heating;	53.9%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + 1-(3-aminopropoxy)-3-methoxybenzene (6451-26-9) → C30H39NO6

Conditions

Yield

Stage #1: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 1-(3-aminopropoxy)-3-methoxybenzene With triethylamine In N,N-dimethyl-formamide at 60℃; for 2.5h; Inert atmosphere;

53%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + ethyl β-alaninate hydrochloride (4244-84-2) → ethyl 3-(11β,17α-dihydroxy-3-oxo-androst-1,4-dien-17β-carboxamido)propionate

Conditions	Yield
Stage #1: (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 8℃; for 16h; Stage #2: ethyl β-alaninate hydrochloride With triethylamine In N,N-dimethyl-formamide at 0 - 8℃; for 16h;	51%

di-p-tolylcarbodiimide (726-42-1) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → (17R)-3'-p-tolyl-11β-hydroxyspiro-2',3,4'-trione

Conditions	Yield
With water In N,N-dimethyl-formamide for 168h; Ambient temperature;	50%

chloroiodoacetyl chloride (827313-06-4) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → 17α-chloroiodoacetoxy-11β-hydroxyandrosta-1,4-dien-3-one-17β-carboxylic acid (750645-43-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2.5h;	49%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + dicyclohexyl-carbodiimide (538-75-0) → (17R)-3'-cyclohexyl-11β-hydroxyspiro-2',3,4'-trione

Conditions	Yield
With water In N,N-dimethyl-formamide for 7h; Ambient temperature;	48%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + Trichloroacetyl chloride (76-02-8) → 17α-trichloroacetoxy-11β-hydroxyandrosta-1,4-dien-3-one-17β-carboxylic acid (750645-44-4)

Conditions	Yield
With potassium hydrogencarbonate In dichloromethane; water for 2h;	48%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride (25952-53-8) → (17R)-2'-ethylimino-11β-hydroxy-3'-dimethylaminopropylspiro-2',3,4'-trione

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Ambient temperature;	47%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + dicyclohexyl-carbodiimide (538-75-0) → (17R)-3'-cyclohexyl-2'-cyclohexylimino-11β-hydroxyspiro-3,4'-dione

Conditions	Yield
With copper dichloride In 1,4-dioxane; acetonitrile for 1h; Ambient temperature;	47%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + ethyl iodide (75-03-6) → ethyl 11β,17α-dihydroxyandrosta-1,4-dien-3-one-17β-carboxylate (182069-13-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	45%

formic acid (64-18-6) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → 17α-formyloxy-11β-hydroxyandrosta-1,4-dien-3-one-17β-carboxylic acid

Conditions	Yield
With acetic anhydride In pyridine for 7h; Heating;	39%

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + chloroacetyl chloride (79-04-9) → 17α-chloroacetoxy-11β-hydroxyandrosta-1,4-dien-3-one-17β-carboxylic acid (750645-47-7)

Conditions	Yield
With potassium hydrogencarbonate In dichloromethane; water for 2h;	26%

diazomethane (186581-53-3, 908094-01-9) + (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) → Δ1-CA-Me (10486-89-2)

Conditions	Yield
In methanol; diethyl ether

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + β‐cyclodextrin (7585-39-9) → 2C42H70O35*C20H26O5

Conditions	Yield
In water at 25℃; for 168h;

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid (37927-29-0) + cyclomaltooctaose (17465-86-0) → 3C48H80O40*2C20H26O5

Conditions	Yield
In water at 25℃; for 168h;

Upstream product

• 50-24-8 prednisolon 
• 15375-21-0 androsta-1,4,9⁽¹¹⁾-triene-3,17-dione 
• 898-84-0 11α-hydroxy-androsta-1,4-diene-3,17-dione 
• 82034-46-6 Loteprednol etabonate 

Downstream Products

• 82034-46-6 Loteprednol etabonate 
• 133991-62-5 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride 
• 1166865-74-2 C₂₇H₃₃NO₅S 
• 1166866-06-3 C₂₇H₃₀N₂O₄S 
• 199331-40-3 etiprednol dicloacetate 

Relevant articles and documents

Preparation method of loteprednol etabonate intermediate

The invention provides a preparation method of a loteprednol etabonate intermediate. The preparation method comprises the following steps: carrying out dehydration reaction on 11 alpha-hydroxyl-ADD and a dehydrating agent in an organic solvent to obtain a compound II; carrying out a first addition reaction on the compound II and a halogenating reagent in an organic solvent in the presence of an acid catalyst, and adding a quenching agent to carry out a quenching reaction after the reaction is finished, so as to obtain a compound III; carrying out reduction reaction on the compound III and a metal reducing agent in an organic solvent in the presence of an acid catalyst to obtain a compound IV; carrying out secondary addition reaction on the compound IV and a cyaniding reagent in an organic solvent in the presence of a basic catalyst to obtain a compound V; and carrying out hydrolysis reaction on thecompound V and an acid reagent in an organic solvent to obtain a compound VI, wherein the compound VI is the loteprednol etabonate intermediate. The preparation method saves energy, reduces consumption, and is easy to operate, high in yield and good in purity.

POTENT SOFT ANTI-INFLAMMATORY CORTICOSTEROID COMPOUNDS AND USES THEROF

Potent soft corticosteroid pharmaceutical compositions comprising them and method for use as anti-inflammatory agents. Also, a method for softening fluticasone propionate and similar corticosteroids to arrive at potent but safer alternatives. The compound S-fluoromethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16a- methyl-3-oxoandrosta-1,4-diene-17β-carbothioate, which is equally potent to but safer than fluticasone, is among those provided. Another compound of particular interest is 2-hydroxyethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16β- methyl-3-oxoandrosta-1,4-diene-17β-carboxylate.

Loteprednol preparation method and ophthalmic composition of loteprednol

The present invention relates to a loteprednol preparation method and an ophthalmic composition of loteprednol, particularly to a loteprednol preparation method, which comprises: dissolving a raw material loteprednol in a first organic solvent to obtain a drug-containing solution, adding a second organic solvent to the obtained solution in a dropwise manner under stirring, continuously stirring, filtering, washing the filter cake by using the second organic solvent, and drying the obtained filter cake in a vacuum oven to obtain the product. The invention further provides a loteprednol bulk drug prepared according to the method, an ophthalmic pharmaceutical composition prepared by using the prepared loteprednol as a bulk drug, and uses of the prepared loteprednol in preparation of drugs for treatment or prevention of ocular inflammations or dry eye. The method of the present invention has excellent pharmaceutical properties, wherein the prepared bulk drug and the preparation have excellent stability.