Acetic Acid → (2S,4S)-2-(2-aminothiazol-4-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 846929노트

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HRID 846929 반응식
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([C:23]2[N:24]=[C:25]([NH2:28])[S:26][CH:27]=2)[CH2:6]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO.ClCCl>[NH2:28][C:25]1[S:26][CH:27]=[C:23]([C@@H:7]2[CH2:6][C@H:5]([SH:4])[CH2:9][N:8]2[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[N:24]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 57011249(2S,4S)-4-acetylthio-(2-aminothiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

생성물 1

HCID 18638803(2S,4S)-2-(2-aminothiazol-4-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine수율 99.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of (2S,4S)-4-acetylthio-2-(2-aminothiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.26 g) in a mixture of methanol (20 ml) and dichloromethane (10 ml) was added sodium methoxide (28% solution in methanol, 1.2 ml) at -30° to -20° C. under an atmosphere of nitrogen. After stirring at 0° C. for 1 hour, acetic acid (0.36 ml) was added to the mixture. The solution was evaporated under reduced pressure, then the residue was dissolved in ethyl acetate, and washed with water, saturated aqueous sodium bicarbonate and brine successively. The dried organic layer was evaporated to give (2S,4S)-2-(2-aminothiazol-4-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.13 g).

후처리

  1. customThe solution was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water, saturated aqueous sodium bicarbonate and brine successively
  4. customThe dried organic layer was evaporated

출처 및 근거

ORD 기록
ord-e59d69fcfdf148e58160eb30ca9b4507
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05138064

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