Water → HCID 13714636, compound

HRID 845213Notes

Reaction equation

HRID 845213 reaction equation
[NH2:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH:4]=[CH:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22].[C:23](OC(=O)C)(=[O:25])[CH3:24].O>N1C=CC=CC=1>[C:23]([NH:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH:4]=[CH:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 13714626HCID 13714626, compound

Product 1

HCID 13714636HCID 13714636, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2.7 g of 4-aminoandrosta-4,6-dien-3,17-dione in 10.8 ml of dry pyridine are added 5.4 ml of acetic anhydride at room temperature dropwise. After 90 minutes of additional stirring, the reaction mixture is cooled to 0° C. and worked up by the addition of cold water, followed by extraction with ethyl acetate. The organic phase is separated, washed with saturated NaCl aqueous solution, dried over Na2SO4 and evaporated in vacuo to yield a residue which is purified by column chromatography on silica gel. Elution with ethyl acetate:methanol 9:1 yields 2.6 g of the title compound as yellow crystals, m.p. 235°-236° C. (dec.);

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. customThe organic phase is separated
  3. washwashed with saturated NaCl aqueous solution
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customto yield a residue which
  7. customis purified by column chromatography on silica gel
  8. washElution with ethyl acetate:methanol 9:1

Sources & evidence

ORD record
ord-9dbe9abcfe524200a9e7f1360412841a
Source dataset
uspto-grants-1988_07
Patent number
US04757061

Reaction notes

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