(2S,5R)-tert-butyl 5-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate → N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)-2,4-dinitrobenzenesulfonamide

HRID 627157노트

반응식

HRID 627157 반응식
[CH2:1]([O:4][N:5]([C@H:21]1[CH2:26][N:25](C(OC(C)(C)C)=O)[C@H:24]([CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH:23]=[CH:22]1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])(=[O:8])=[O:7])[CH:2]=[CH2:3]>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[CH2:1]([O:4][N:5]([C@@H:21]1[CH:22]=[CH:23][C@@H:24]([CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[NH:25][CH2:26]1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19])(=[O:8])=[O:7])[CH:2]=[CH2:3]

참가 물질

4

반응물 1

HCID 89852173(2S,5R)-tert-butyl 5-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate2회

생성물 1

HCID 89852376N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)-2,4-dinitrobenzenesulfonamide수율 106.7%

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of (2S,5R)-tert-butyl 5-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 126, 19.5 g, 31.01 mmol) in DCM (250 mL) under nitrogen at rt, zinc bromide (20.95 g, 93.04 mmol) was added. The reaction mixture was stirred at rt for 6 hs, (lcms indicated the reaction was a clean one) and diluted with 50 mL DCM and washed with sat. NaHCO3, brine, dried over MgSO4, filtered and concentrated to give the desired product as an orange oil (17.5 g).

후처리

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d870f3198aee46e19a6861356ce26ca4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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