p-Toluenesulfonic acid → 11beta-Fluoro-17beta-(4-sulfamoylbenzoxy)-7alpha-methylestr-4-en-3-one

HRID 855481Notes

Reaction equation

HRID 855481 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1.[S:23]([C:27]1[CH:35]=[CH:34][C:30]([C:31](O)=O)=[CH:29][CH:28]=1)(=[O:26])(=[O:25])[NH2:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[O:20][CH2:31][C:30]2[CH:34]=[CH:35][C:27]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:28][CH:29]=2)[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8739CarzenideHCID 516892Sodium BicarbonateHCID 990463811beta-Fluoro-17beta-hydroxy-7alpha-methylestr-4-en-3-one

Product 1

HCID 6933350111beta-Fluoro-17beta-(4-sulfamoylbenzoxy)-7alpha-methylestr-4-en-3-oneYield 38.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 500 mg of 11β-fluoro-17β-hydroxy-7α-methylestr-4-en-3-one in 7.5 ml of pyridine was mixed at room temperature with 750 mg of 4-sulfamoylbenzoic acid, 800 mg of N,N-dicyclohexylcarbodiimide as well as 125 mg of p-toluenesulfonic acid and stirred for 8.5 hours. Then, it was added to sodium bicarbonate solution, extracted four times with dichloromethane, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum, and chromatographed on silica gel with dichloromethane/acetone. 302 mg of 11β-fluoro-17β-(4-sulfamoylbenzoxy)-7α-methylestr-4-en-3-one with a melting point of 232° C. was obtained. [α]D=+100.5° (CHCl3).

Workup

  1. extractionextracted four times with dichloromethane
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customchromatographed on silica gel with dichloromethane/acetone

Sources & evidence

ORD record
ord-d819f2bb45e44f0fb83e7fec939fb424
Source dataset
uspto-grants-2007_08
Patent number
US07262023B2

Reaction notes

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