Ethyl Acetate → (2S,4R)-4-methanesulfonyloxy-2-(2-methylthiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1649801노트

반응식

HRID 1649801 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]([NH2:31])(=[S:30])[CH3:29].C(OCC)(=O)C>CO.ClCCl>[CH3:14][S:11]([O:10][C@H:8]1[CH2:7][N:6]([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])[C@H:5]([C:3]2[N:31]=[C:28]([CH3:29])[S:30][CH:2]=2)[CH2:9]1)(=[O:12])=[O:13]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 2723949ThioacetamideHCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

생성물 1

HCID 14305073(2S,4R)-4-methanesulfonyloxy-2-(2-methylthiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine수율 74.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.15 g) in a mixture of methanol (20 ml) and dichloromethane (15 ml) was added thioacetamide (388 mg) at room temperature. After stirring at the same temperature for 4 hours, the mixture was poured into ethyl acetate and washed in turn with saturated aqueous sodium bicarbonate and brine. The dried organic layer was evaporated and the resulting oil was subjected to a column chromatography on silica gel (50 g) eluting with a mixture of acetone and dichloromethane (1:20 V/V) to give (2S,4R)-4-methanesulfonyloxy-2-(2-methylthiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (810 mg).

후처리

  1. washwashed in turn with saturated aqueous sodium bicarbonate and brine
  2. customThe dried organic layer was evaporated
  3. washeluting with a mixture of acetone and dichloromethane (1:20 V/V)

출처 및 근거

ORD 기록
ord-b5728b1183894a978d58993464e4cc0a
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921852

반응 노트

불러오는 중…