Methanol → 1-benzyl-4-tert-butyloxycarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

HRID 1106923노트

반응식

HRID 1106923 반응식
[O:1]=[O+][O-].[CH2:4]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)C2[CH2:20][CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][C:12]1=2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CSC.[CH3:34][OH:35]>>[CH2:4]([N:11]1[C:19]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:34](=[O:35])[CH2:20][CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][C:12]1=[O:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 183772769-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

생성물 1

HCID 187882101-benzyl-4-tert-butyloxycarbonyl-2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

실험 절차

Ozone was bubbled through a solution of 9-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (6.0 g, 16.6 mmol) in methanol (90 ml) at -78° C. until a blue colour persisted. Nitrogen was then bubbled through the solution until clear, followed by the addition of dimethyl sulphide (12.0 ml, 163 mmol). The solution was allowed to warm to room temperature and stirring continued for a further 2 hours, followed by evaporation to dryness. The crude product was purified by chromatography on silica gel with ethyl acetate-hexane (1:1) as eluant. (6.0 g, 92%).

후처리

  1. customNitrogen was then bubbled through the solution until clear,
  2. customfollowed by evaporation to dryness
  3. customThe crude product was purified by chromatography on silica gel with ethyl acetate-hexane (1:1) as eluant

출처 및 근거

ORD 기록
ord-fd39eb218a3e4c4db035490fd4636796
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057311

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