Acetic Acid → HCID 13276358, compound

HRID 904862Notes

Reaction equation

HRID 904862 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:29])[C:19]2([S:26][CH2:27][CH3:28])[S:23][CH2:24][CH3:25])[C@H:15]2[C@@:6]1([F:32])[C@:7]1([CH3:31])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:30])[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:29])[C:19]2([S:23][CH2:24][CH3:25])[S:26][CH2:27][CH3:28])[C@H:15]2[C@@:6]1([F:32])[C@:7]1([CH3:31])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:30])[CH:9]=[CH:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 86739144HCID 86739144, compound

Product 1

HCID 13276358HCID 13276358, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 11β-(acetyloxy)-17,17-bis-(ethylthio)-9-fluoro-16α-hydroxyandrosta-1,4-dien-3-one (100 mg, 0.207 mmole) in a mixture of dry dimethylsulfoxide (2.0 ml), acetic anhydride (0.7 ml) and acetic acid (0.1 ml) was left standing at room temperature for 18 hours. The mixture was then added to water and was extracted with chloroform. The chloroform solution was washed with water, dried (MgSO4) and evaporated to afford the title compound (94 mg) as a solid.

Workup

  1. waitwas left
  2. extractionwas extracted with chloroform
  3. washThe chloroform solution was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-e34a05aadf064d4393d48ba618d1ce19
Source dataset
uspto-grants-1983_12
Patent number
US04420428

Reaction notes

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