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

HRID 846929ノート

反応式

HRID 846929 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-e59d69fcfdf148e58160eb30ca9b4507
出典データセット
uspto-grants-1992_08
特許番号
US05138064

反応ノート

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