p-Toluenesulfonic acid → HCID 70464278, compound

HRID 2296031Notes

Reaction equation

HRID 2296031 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH:4]=[CH:5][C:6](=[O:22])[CH:7]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[C:24]([O:20][C@H:19]1[CH2:18][C@@:16]2([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]2=[O:21])[C@H:11]2[C@@:2]1([F:1])[C@:3]1([CH3:23])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:6](=[O:22])[CH:5]=[CH:4]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 13421116HCID 13421116, compound

Product 1

HCID 70464278HCID 70464278, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 20 g of 9-fluoro-11β-hydroxyandrosta-1,4-dien-3,17-dione, 120 ml of glacial acetic acid, 120 ml of acetic anhydride and 5 g of p-toluenesulfonic acid was stirred at room temperature under nitrogen for 20 hours. The resulting solution was quenched with 5 g of sodium acetate. The solvent was partially removed in vacuo at 35°-40° C. and the resultant slurry was diluted with chloroform. The chloroform solution was washed with water, saturated sodium bicarbonate and water, dried over anhydrous sodium sulfate and evaporated in vacuo to give the title compound. This was crystallized from ethyl acetate-hexane to give 20 g of the title compound melting point 177°-178° C.

Workup

  1. customThe resulting solution was quenched with 5 g of sodium acetate
  2. customThe solvent was partially removed in vacuo at 35°-40° C.
  3. additionthe resultant slurry was diluted with chloroform
  4. washThe chloroform solution was washed with water, saturated sodium bicarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-712b4d363a464ae990eaf484a22ed61c
Source dataset
uspto-grants-1984_01
Patent number
US04427592

Reaction notes

Loading…