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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Methyl morpholine oxide → allyl(1R,5S,6S)-2-((3S,5S)-1-allyloxycarbonyl-5-formylpyrrolidin-3-yl)thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate

HRID 568227
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HRID 568227 반응식
[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][OH:13])[CH2:10][C@H:9]([S:14][C:15]2[C@H:16]([CH3:39])[C@@H:17]3[C@@H:27]([C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH3:29])[C:26](=[O:38])[N:18]3[C:19]=2[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:8]1)=[O:6])[CH:2]=[CH2:3].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([NH3+])CC.C([NH3+])CC.C([NH3+])CC.C([NH3+])CC.[Ru]([O-])(=O)(=O)=O.[Ru]([O-])(=O)(=O)=O.[Ru]([O-])(=O)(=O)=O>[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH:12]=[O:13])[CH2:10][C@H:9]([S:14][C:15]2[C@H:16]([CH3:39])[C@@H:17]3[C@@H:27]([C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH3:29])[C:26](=[O:38])[N:18]3[C:19]=2[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 82029Methyl morpholine oxideHCID 131722312HCID 131722312, 화합물

생성물 1

HCID 131722311allyl(1R,5S,6S)-2-((3S,5S)-1-allyloxycarbonyl-5-formylpyrrolidin-3-yl)thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate수율 82.8%

시약·촉매·용매 2

HCID 178458035HCID 178458035, 화합물촉매
HCID 6344
Dichloromethane
용매

실험 절차

Tetrakis(n-propylammonium) perruthenate (VII) (45 mg) is added a solution of 871 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(hydroxymethyl)pyrrolidin-3-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate, 272 mg of N-methylmorpholine N-oxide, and 750 mg of 4A active molecular sieves (powder) in 3 ml of dry dichloromethane, and the mixture is stirred in an argon atmosphere at room temperature for 10 min. The reaction solution as such is purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give 719 mg of allyl(1R,5S,6S)-2-((3S,5S)-1-allyloxycarbonyl-5-formylpyrrolidin-3-yl)thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate as a colorless viscous material.

후처리

  1. customThe reaction solution as such is purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-b47ceed8271d45ec880d65167504b533
출처 데이터셋
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06180622B2

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