5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate

Base Information

• Chemical Name: 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate
• CAS No.: 80474-67-5
• Molecular Formula: C25H31F2IO5S
• Molecular Weight: 608.485
• Mol file: 80474-67-5.mol

Synonyms:5-Iodomethyl 6α,9α-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)-androsta-1,4-diene-17β-carbothioate;5-IODOMETHYL 6A,9A-DIFLUORO-11B-HYDROXY-16A-METHYL-3-OXO-17A-(PROPIONYLOXY)-ANDROSTA-1,4-DIENE-17B-CARBOTHIOATE;5-IODOMETHYL 6A,9A-DIFLUORO-11SS-HYDROXY-16A-METHYL-3-OXO-17A-(PROPIONYLOXY)-ANDROSTA-1,4-DIENE-17SS-CARBOTHIOATE;

Chemical Property of 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 606.721°C at 760 mmHg
• Flash Point: 320.733°C
• PSA: 105.97000
• Density: 1.553g/cm³
• LogP: 4.89550
• Solubility.: Chloroform, Dichloromethane, DMF, Ethanol, Ethyl Acetate, Methanol

Purity/Quality:

95%, ^*data from raw suppliers

5-Iodomethyl6α,9α-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)-androsta-1,4-diene-17β-carbothioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the synthesis of Fluticasone Propionate An intermediate in the synthesis of Fluticasone Propionate.

Technology Process of 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate

There total 10 articles about 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate 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: 90.1%

S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate (80486-69-7) → S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate (80474-67-5)

Guidance literature:

With sodium iodide; In acetone; for 2h; Heating;

DOI:10.1002/(SICI)1099-1344(199707)39:7<567::AID-JLCR999>3.0.CO;2-P

Reference yield: 75.0%

→ S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate (80474-67-5)

Guidance literature:

With acetic acid; In ethyl acetate; at 0 - 85 ℃; for 1h; Purification / work up;

Reference yield:

Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(toluene-4-sulfonyloxymethylsulfanylcarbonyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (192191-50-7) → flixotide (80474-14-2) + S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate (80474-67-5) + C49H60F4O10S2

Guidance literature:

With potassium fluoride; aminopolyether 2.2.2; potassium iodide; In acetonitrile; at 100 ℃; for 0.583333h; under 1050.08 Torr;

DOI:10.1002/(SICI)1099-1344(199707)39:7<567::AID-JLCR999>3.0.CO;2-P

upstream raw materials:

S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate

Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(toluene-4-sulfonyloxymethylsulfanylcarbonyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid

Downstream raw materials:

flixotide

Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(toluene-4-sulfonyloxymethylsulfanylcarbonyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

Refernces

• 1、 -. "NOVEL PROCESS AND INTERMEDIATES". Page/Page column 21; 29-30. . Retrieved 2008/06/13.
• 2、 Phillipps,Bailey,Bain,Borella,Buckton,Clark,Doherty,English,Fazakerley,Laing,Lane-Allman,Robinson,Sandford,Sharratt,Steeples,Stonehouse,Williamson. "Synthesis and structure-activity relationships in a series of antiinflammatory corticosteroid analogues, halomethyl androstane-17β- carbothioates and -17β-carboselenoates". . p. 3717 - 3729. Retrieved 2007/10/02.