Water → 4-acetamido-N-(1,1-dimethylethyl)-3-oxoandrosta-4,6-diene-17beta-carboxamide

HRID 654353Notes

Reaction equation

HRID 654353 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@@H:10]2[C:22]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].O.[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([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@@H:10]2[C:22]([NH:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 677532974-amino-N-(1,1-dimethylethyl)-3-oxoandrosta-4,6-diene-17beta-carboxamide

Product 1

HCID 677530884-acetamido-N-(1,1-dimethylethyl)-3-oxoandrosta-4,6-diene-17beta-carboxamideYield 30.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-amino-N-(1,1-dimethylethyl)-3-oxoandrosta-4,6-diene-17β-carboxamide (0.9 g, 2.34 mmole) in acetic anhydride (3 mL) and pyridine (6 mL) was stirred overnight at room temperature. Water was added and the mixture was stirred for 3 hours. The solids were collected by filtration to give a brown solid which was purified by flash chromatography (hexane-50% ethyl acetate, ethyl acetate) to give 4-acetamido-N-(1,1-dimethylethyl)-3-oxoandrosta-4,6-diene-17β-carboxamide (0.29 g, 30.4%, diethyl ether-hexane). IR 3442, 3382, 1664, 1616 cm-1 ; MS (CI) m/z 427 (100%, M+ +1); (EI) m/z 426 (65%, M+), 57 (100%); 1H NMR (CDCl3) δ 0.78 (3H, s, C18 -Me), 1.13 (3H, s, C19 -Me), 1.35 (s, 3× tBu-Me's), 2.14 (s, Ac-Me), 5.13 (1H, s, NHCOBu), 6.16 (2H, s, C6 -H+C7 -H), 7.12 (1H, NHAc); 13C NMR (CDCl3) δ 124.65, 124.89, 139.95, 153.20, 168.74, 171.44, 194.93. This compound has the following structure: ##STR4##

Workup

  1. filtrationThe solids were collected by filtration
  2. customto give a brown solid which
  3. customwas purified by flash chromatography (hexane-50% ethyl acetate, ethyl acetate)

Sources & evidence

ORD record
ord-ad4c5e8edf9b4026bcd5a0b904d81e65
Source dataset
uspto-grants-1992_07
Patent number
US05130424

Reaction notes

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