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

HRID 37256ノート

反応式

HRID 37256 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-7f82053ae2c840378d717a7ac8c6b8eb
出典データセット
uspto-grants-1995_05
特許番号
US05420122

反応ノート

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