Acetic Acid → HCID 13276350, compound

HRID 904860Notes

Reaction equation

HRID 904860 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][C@@H:18]([OH:27])[C:19]2([S:25][CH3:26])[S:23][CH3:24])[C@H:15]2[C@@:6]1([F:30])[C@:7]1([CH3:29])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:28])[CH:9]=[CH:8]1)(=[O:3])[CH3:2].CS(C)=O.C(OC(=O)C)(=O)C.C(O)(=O)C>O>[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][C:18](=[O:27])[C:19]2([S:23][CH3:24])[S:25][CH3:26])[C@H:15]2[C@@:6]1([F:30])[C@:7]1([CH3:29])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:28])[CH:9]=[CH:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 13276348HCID 13276348, compound

Product 1

HCID 13276350HCID 13276350, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.0 g (6.6 mmole) of 11β-(acetyloxy)-9-fluoro-16α-hydroxy-17,17-bis(methylthio)androsta-1,4-dien-3-one in a solution of dry dimethylsulfoxide (30 ml), acetic anhydride (20 ml) and glacial acetic acid (10 ml) was stirred at room temperature under nitrogen overnight. The resulting solution was poured into cold water and extracted with dichloromethane. The dichloromethane solution was washed with saturated sodium bicarbonate solution and water, dried over anhydrous Na2SO4 and evaporated in vacuo to give 2.9 g of solid, melting point 225°-227° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane solution was washed with saturated sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-75c00f73e13945438b41a149d526c1e0
Source dataset
uspto-grants-1983_12
Patent number
US04420428

Reaction notes

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