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

HRID 1109000노트

반응식

HRID 1109000 반응식
[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]

참가 물질

7

반응물 3

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2회HCID 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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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 hexane-40% 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,5β- and 4β,5β-isomers and it was used as is in further reactions.

후처리

  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 hexane-40% ethyl acetate)

출처 및 근거

ORD 기록
ord-910f32eaa0fb441abf030663bf6d6ac1
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318961

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