(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one

Base Information

• Chemical Name: (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one
• CAS No.: 1323943-47-0
• Molecular Formula: C₃₀H₃₃F₄NO₃
• Molecular Weight: 531.591

Synonyms:(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one

Chemical Property of (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one

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Technology Process of (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one

There total 10 articles about (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one 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: 32.3%

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-(2-fluoro-acetyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one hydrochloride (1323943-46-9) + 4-Fluorobenzyl bromide (459-46-1) → (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one (1323943-47-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

Reference yield:

difluprednate → (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one (1323943-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium acetate / N,N-dimethyl-formamide / 1.5 h / 100 °C / Inert atmosphere

2.1: ethanol / Candida antarctica lipase / 37 °C / Enzymatic reaction

3.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / acetonitrile / 0.5 h / 20 °C / Inert atmosphere

3.2: 4 h / 60 °C

4.1: trifluoroacetic acid / 1,4-dioxane / 1 h / 100 °C / Closed vessel

5.1: sodium hydrogencarbonate / acetonitrile / 1 h / 50 °C

6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 5 h / 20 °C

7.1: triethylamine / dichloromethane / 20 °C

With hydrogenchloride; ethanol; potassium acetate; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; Candida antarctica lipase; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-17-(2-fluoroacetyl)-11-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthren-3-one (1270041-07-0) → (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-6b-(2-fluoro-acetyl)-8-(4-fluoro-benzyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one (1323943-47-0)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / 1,4-dioxane / 1 h / 100 °C / Closed vessel

2: sodium hydrogencarbonate / acetonitrile / 1 h / 50 °C

3: hydrogenchloride / dichloromethane; 1,4-dioxane / 5 h / 20 °C

4: triethylamine / dichloromethane / 20 °C

With hydrogenchloride; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; acetonitrile;

upstream raw materials:

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-(2-fluoro-acetyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one hydrochloride

4-Fluorobenzyl bromide

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzyl-4b,12-difluoro-6b-(2-fluoro-acetyl)-5-hydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-(2-fluoro-ace tyl) -5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,6b,7,9,9a,10,10a,10b, 11,12- tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthrene-8-carboxylic acid vinyl ester

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