Hydrogen Peroxide → N-(1,1-Dimethylethyl)-4,5-epoxy3-oxoandrostane-17beta-carboxamide

HRID 2082409ノート

反応式

HRID 2082409 の反応式
[CH3:1][C:2]([NH:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=[O:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)=[O:7])([CH3:4])[CH3:3].[OH:28]O.[OH-].[Na+]>CO.ClCCl.O>[CH3:4][C:2]([NH:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C:17]2([O:28][CH:18]2[C:19](=[O:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)=[O:7])([CH3:1])[CH3:3]

参加物

7

反応物 3

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2 回HCID 475445(8S,9S,10R,13S,14S,17S)-N-tert-butyl-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxamide

生成物 1

HCID 86745913N-(1,1-Dimethylethyl)-4,5-epoxy3-oxoandrostane-17beta-carboxamide収率 66.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of N-(1,1-dimethylethyl)-3-oxoandrost-4-ene-17β-carboxamide (4.77 g, 12.8 mmole) in methanol (55 mL) and dichloromethane (11 mL) was cooled to 12° C. and treated in one portion with 30% aqueous hydrogen peroxide (3.3 mL) followed by dropwise addition of an aqueous sodium hydroxide solution prepared by dissolving sodium hydroxide (0.38 g) in water (2.2 mL). After one hour, the cooling bath was removed and the reaction was stirred for an additional 3 hours. Most of the solvent was then removed in vacuo. The residue was dissolved in dichloromethane and purified by flash chromatography (hexane-20% ethyl acetate and hexane40% ethyl acetate) to give N-(1,1-Dimethylethyl)-4,5-epoxy-3-oxoandrostane-17β-carboxamide (3.3 g, 66.2%) as a solid foam. This material was a mixture of the 4α, 5α- and 4β, 5β-isomers and it was used as is in further reactions.

後処理

  1. customprepared
  2. customthe cooling bath was removed
  3. customMost of the solvent was then removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. custompurified by flash chromatography (hexane-20% ethyl acetate and hexane40% ethyl acetate)

出典と根拠

ORDレコード
ord-8735c0878d8747d193d3933b4eb24806
出典データセット
uspto-grants-1993_02
特許番号
US05189032

反応ノート

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