Acetate → Galeterone

HRID 59055Notes

Reaction equation

HRID 59055 reaction equation
C([O-])(=O)C.C([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH:17]=[C:18]2[N:28]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[N:30]=[CH:29]2)[CH2:10]1)(=O)C.[OH-].[K+]>CO>[OH:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH:17]=[C:18]2[N:28]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[N:30]=[CH:29]2)[CH2:10]1

Participants

5

Reactant 3

HCID 175AcetateHCID 14797Potassium HydroxideHCID 11464592(3S,8R,9S,10R,13S,14S)-17-(1H-Benzo[D]imidazol-1-YL)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[A]phenanthren-3-YL acetate

Product 1

HCID 11188409Galeterone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 5 prepared by following general method C, treating acetate solution of 15 (1 g 3.02 mmol) in methanol (15 mL) with 10% methanolic KOH (5 mL) for 1.5 h. Purification by FCC over short column provided pure 5 with identical spectral and analytical data as we previously reported.

Workup

  1. customPurification by FCC over short column
  2. customprovided pure 5 with identical spectral and analytical data as we

Sources & evidence

ORD record
ord-219de467e34b4d72ad05d9e2ef510967
Source dataset
uspto-grants-2016_09
Patent number
US09439912B2

Reaction notes

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