Water → HCID 22839713, compound

HRID 622341Notes

Reaction equation

HRID 622341 reaction equation
[NH2:1][C@@H:2]1[C:19]2[C@:14]([CH3:21])([CH:15]=[CH:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.[OH2:23].N1[CH:29]=[CH:28]C=CC=1>C(OC(=O)C)(=O)C>[C:28]([NH:1][C@@H:2]1[C:19]2[C@:14]([CH3:21])([CH:15]=[CH:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1)(=[O:23])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 54573576HCID 54573576, compound

Product 1

HCID 22839713HCID 22839713, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6α-amino androsta-1,4-diene-3,17-dione (1,4 g) in 5.5 ml of dry pyridine, 2.8 ml of acetic anhydride are added dropwise at room temperature. The solution is stirred for 90 minutes and then water is dropped into the cooled (0° C.) solution. After 10 minutes stirring the reaction mixture is extracted with five 100 ml portions of ethyl acetate which are collected and dried over anhydrous sodium sulphate. The solvent is then removed in vacuum to yield a crude which is purified by chromatography on silica gel so obtaining 1.30 g of pure 6α-acetylamino androsta-1,4-diene-3,17-dione;

Workup

  1. stirringAfter 10 minutes stirring the reaction mixture
  2. extractionis extracted with five 100 ml portions of ethyl acetate which
  3. customare collected
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent is then removed in vacuum
  6. customto yield a crude which
  7. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a000c901c8834d5e93e85d8f2c62be34
Source dataset
uspto-grants-1988_09
Patent number
US04771043

Reaction notes

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