Ethyl Acetate → HCID 57303896, 화합물

HRID 1649829

반응식

HRID 1649829 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.[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]([NH2:39])=[S:38])=[O:34])([CH3:31])([CH3:30])[CH3:29].C(OCC)(=O)C>CO.ClCCl>[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]1[S:38][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:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[N:39]=1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 5324304tert-butyl N-(carbamothioylmethyl)carbamateHCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

생성물 1

HCID 57303896HCID 57303896, 화합물수율 40.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (20 g) in a mixture of methanol (200 ml) and dichloromethane (200 ml) was added 2-(N-t-butoxycarbonylamino)thioacetamide (20 g) at room temperature. After stirring at ambient temperature for 12 hours, the mixture was poured into ethyl acetate, washed with saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated, and the obtained oil was subjected to a column chromatography on silica gel and eluted with a mixture of acetone and dichloromethane (1:5, V/V) to give (2S,4R)-2-[2-(N-t-butoxycarbonylamino)methylthiazol-4-yl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (9.7 g).

후처리

  1. washwashed with saturated sodium bicarbonate and brine successively
  2. customThe dried organic layer was evaporated
  3. washeluted with a mixture of acetone and dichloromethane (1:5, V/V)

출처 및 근거

ORD 기록
ord-fc8e683591ae4dfc80bc240d51c1adba
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921852

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