Imidazole → 7-[O-{3-(imidazol-1-yl)propyl}oximino]-5-androstene-3beta,17beta-diol diacetate

HRID 1808757Notes

Reaction equation

HRID 1808757 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[N:28][O:29][CH2:30][CH2:31][CH2:32]Cl)[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[CH2:6]1)(=[O:3])[CH3:2].[NH:34]1[CH:38]=[CH:37][N:36]=[CH:35]1>>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[N:28][O:29][CH2:30][CH2:31][CH2:32][N:34]3[CH:38]=[CH:37][N:36]=[CH:35]3)[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:24][C:25](=[O:27])[CH3:26])[CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 795ImidazoleHCID 867617547-[O-(3-chloropropyl)oximino]-5-androstene-3beta,17beta-diol diacetate

Product 1

HCID 867617557-[O-{3-(imidazol-1-yl)propyl}oximino]-5-androstene-3beta,17beta-diol diacetate

Procedure

A mixture of 7-[O-(3-chloropropyl)oximino]-5-androstene-3β,17β-diol diacetate (23) (1 g, 2.08 mmol) and powdered imidazole (1.5 g) was fused at 110-120° C. for 5 h. The completion of reaction was monitored by TLC. The reaction was quenched with iced water to afford a the product 7-[O-{3-(imidazol-1-yl)propyl}oximino]-5-androstene-3β,17β-diol diacetate (24)

Workup

  1. customThe completion of reaction
  2. customThe reaction was quenched with iced water

Sources & evidence

ORD record
ord-e27759a7ed8543b88fae50bf12671cc4
Source dataset
uspto-grants-2013_01
Patent number
US08361996B2

Reaction notes

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