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Ethyl Acetate → (2S,4R)-2-[2-(dimethoxymethyl)thiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1649822
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HRID 1649822 반응식
Br[CH2:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16])=O.[CH3:28][O:29][CH:30]([O:34][CH3:35])[C:31]([NH2:33])=[S:32].C(OCC)(=O)C>CN(C)C(=O)C.ClCCl>[CH3:28][O:29][CH:30]([O:34][CH3:35])[C:31]1[S:32][CH:2]=[C:3]([C@@H:5]2[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]2[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[N:33]=1
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참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineHCID 199345072,2-Dimethoxyethanethioamide

생성물 1

HCID 15077761(2S,4R)-2-[2-(dimethoxymethyl)thiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine수율 60.3%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 31374Dimethylacetamide용매

실험 절차

To a solution of (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.0 g) in a mixture of N,N-dimethylacetamide (10 ml) and dichloromethane (5 ml) was added 2,2-dimethoxythioacetamide (1.28 g) at room temperature. After stirring at room temperature for 12 hours, the mixture was poured into ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate and brine successively, dried over magnesium sulfate, and evaporated. The obtained oil was subjected to a column chromatography on silica gel and eluted with a mixture of dichloromethane and acetone (20:1, V/V) to give (2S,4R)-2-[2-(dimethoxymethyl)thiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.6 g).

후처리

  1. washThe organic layer was washed with water, saturated sodium bicarbonate and brine successively
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. washeluted with a mixture of dichloromethane and acetone (20:1, V/V)

출처 및 근거

ORD 기록
ord-1b5504c4309a4d39a934878112a76676
출처 데이터셋
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04921852

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