Temocapril hydrochloride

Base Information

• Chemical Name: Temocapril hydrochloride
• CAS No.: 110221-44-8
• Molecular Formula: C23H28N2O5S2^.HCl
• Molecular Weight: 513.079
• Hs Code.: 2934999090
• UNII: 8G820I95VP
• DSSTox Substance ID: DTXSID7046914
• Wikidata: Q27270390
• NCI Thesaurus Code: C99556
• ChEMBL ID: CHEMBL2104499
• Mol file: 110221-44-8.mol

Synonyms:alpha-((2S,6R)-6-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl)acetic acid.HCl;CS 622;CS-622;CS622;temocapril;temocapril hydrochloride

Chemical Property of Temocapril hydrochloride

Chemical Property:

• Appearance/Colour: white solid powder
• Vapor Pressure: 1.34E-21mmHg at 25°C
• Melting Point: 196-200 °C
• Refractive Index: 1.628
• Boiling Point: 717.4 °C at 760 mmHg
• Flash Point: 387.7 °C
• PSA: 153.42000
• Density: 1.33g/cm³
• LogP: 1.28460
• Storage Temp.: -20°C Freezer
• Solubility.: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 512.1206421
• Heavy Atom Count: 33
• Complexity: 644

Purity/Quality:

99% ^*data from raw suppliers

TemocaprilHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC2CSC(CN(C2=O)CC(=O)O)C3=CC=CS3.Cl
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CS[C@@H](CN(C2=O)CC(=O)O)C3=CC=CS3.Cl
• Description: Temocapril is a novel ACE inhibitor marketed in Japan for the treatment of hypertension. Temocapril is three times more potent than enalapril by oral administration, and has a long duration of action. It is characterized by a rapid onset of action resulting from a fast conversion of temocapril to the active metabolite diacid. Unlike most ACE inhibitors which are excreted mainly through the kidneys, temocapril is excreted predominantly through the biliary route indicating that temocapril is especially useful for treating hypertensive patients with renal dysfunction. The potential usefulness of temocapril in the treatment of congestive heart failure has been reported.
• Uses: Angiotensin-converting enzyme (ACE) inhibitor. Hydrolyzed in vivo to the active diacid metabolite. Angiotensin-converting enzyme (ACE) inhibitor. Hydrolyzed in vivo to the active diacid metabolite angiotensin-converting enzyme inhibitor (ACE-I)

Technology Process of Temocapril hydrochloride

There total 13 articles about Temocapril hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

(S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester (110221-37-9) → temocapril Hydrochloride (110221-44-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 16h; Ambient temperature;

DOI:10.1021/jm00394a009

Reference yield:

ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5) → temocapril Hydrochloride (110221-44-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 80 percent / Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

3: 94 percent / NaH / dimethylformamide / 5 h / Ambient temperature

4: 78 percent / 4 N aq. HCl / dioxane / 16 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydride; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a009

Reference yield:

1-(2-thienyl)-2-nitroethene (34312-77-1) → temocapril Hydrochloride (110221-44-8)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine / toluene / 16 h / Ambient temperature

2: 64 percent / H₂, AcOH / 5percent Pd/C / 5 h / 70 °C / 2280 Torr

3: 69 percent / diphenyl phosphorazidate, N-methylmorpholine / dimethylformamide / 16 h / Ambient temperature

4: 35 percent / 4 N aq. HCl / dioxane / 4 h / Ambient temperature

5: 80 percent / Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

6: 94 percent / NaH / dimethylformamide / 5 h / Ambient temperature

7: 78 percent / 4 N aq. HCl / dioxane / 16 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; diphenyl phosphoryl azide; hydrogen; sodium hydride; acetic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00394a009

upstream raw materials:

(S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester

1-(2-thienyl)-2-nitroethene

(E)-2-oxo-4-phenyl-3-butenoic acid

R-2-hydroxy-4-phenylbutyric acid L-menthyl ester

Downstream raw materials:

[3H]-Temocaprilat

(S)-temocapril sulfoxide hydrochloride

(R)-temocapril sulfoxide hydrochloride

Refernces