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

HRID 37250노트

반응식

HRID 37250 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 (308 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-490feb2bd1d54045b19de205d9cea90f
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420122

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