Pregna-1,4-diene-3,20-dione,9-fluoro-11,17-dihydroxy-21,21-diiodo-16-methyl-, (11b,16b)- (9CI)

Base Information

• Chemical Name: Pregna-1,4-diene-3,20-dione,9-fluoro-11,17-dihydroxy-21,21-diiodo-16-methyl-, (11b,16b)- (9CI)
• CAS No.: 37414-01-0
• Molecular Formula: C22H27 F I2 O4
• Molecular Weight: 628.261
• Mol file: 37414-01-0.mol

Synonyms:9-Fluoro-11b,17-dihydroxy-21,21-diiodo-16b-methylpregna-1,4-diene-3,20-dione

Chemical Property of Pregna-1,4-diene-3,20-dione,9-fluoro-11,17-dihydroxy-21,21-diiodo-16-methyl-, (11b,16b)- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pregna-1,4-diene-3,20-dione,9-fluoro-11,17-dihydroxy-21,21-diiodo-16-methyl-, (11b,16b)- (9CI)

There total 14 articles about Pregna-1,4-diene-3,20-dione,9-fluoro-11,17-dihydroxy-21,21-diiodo-16-methyl-, (11b,16b)- (9CI) 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: 100.0%

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione (1879-77-2) → (8S,9R,10S,11S,13S,14S,16S,17R)-17-(2,2-Diiodo-acetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one (37414-01-0)

Guidance literature:

With iodine; calcium chloride; calcium oxide; In methanol; at 25 - 27 ℃; for 1h;

DOI:10.1080/00397910500464855

Reference yield:

16α,17α-epoxy-3β-hydroxy-5α-pregn-9(11)-en-20-one (884488-47-5) → (8S,9R,10S,11S,13S,14S,16S,17R)-17-(2,2-Diiodo-acetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one (37414-01-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / pyridine / 20 °C

2.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH₂Cl₂ / 20 h / 20 °C

3.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C

4.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating

4.2: 50 percent / p-toluenesulfonic acid / CH₂Cl₂ / 4 h / 20 °C

5.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling

5.2: 75.8 percent / sodium hydroxide / CH₂Cl₂; methanol; H₂O / 2 h / cooling

6.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH₂Cl₂ / 5 h / -70 - 0 °C

7.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C

With pyridine; perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 3-iodosylbenzoic acid; diphenyl diselenide; hydrogen fluoride; iodine; toluene-4-sulfonic acid; orthoformic acid triethyl ester; calcium chloride; calcium oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1080/00397910500464855

Reference yield:

16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione (37413-99-3) → (8S,9R,10S,11S,13S,14S,16S,17R)-17-(2,2-Diiodo-acetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one (37414-01-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH₂Cl₂ / 5 h / -70 - 0 °C

2: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C

With hydrogen fluoride; iodine; calcium chloride; calcium oxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1080/00397910500464855

upstream raw materials:

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

16α,17α-epoxy-3β-hydroxy-5α-pregn-9(11)-en-20-one

16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione

16β-methyl-3β,17α-dihydroxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene

Downstream raw materials:

betamethasone

betamethasone 21-acetate

Refernces