Sodium Chloride → (2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

HRID 5100

反応式

HRID 5100 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][SH:10])=[CH:7][CH:6]=1.[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23](OS(C)(=O)=O)[CH2:22][C@H:21]1[C:30](=[O:34])[NH:31][CH2:32][CH3:33])=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl-].[Na+]>CN(C)C=O>[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23]([S:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[CH2:22][C@H:21]1[C:30](=[O:34])[NH:31][CH2:32][CH3:33])=[O:19])([CH3:16])([CH3:15])[CH3:14]

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 57182446(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-methanesulfonyloxypyrrolidine

生成物 1

HCID 14880290(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

3.57 g of sodium hydride (as a 55% w/w suspension in mineral oil) was added, whilst ice-cooling, to a solution of 11.31 ml of 4-methoxybenzyl mercaptan dissolved in 150 ml of dry dimethylformamide and the mixture was stirred at 0° to 5° C. for 30 minutes. A solution of 26.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-methanesulfonyloxypyrrolidine in 100 ml of dry dimethylformamide was then added to the resulting mixture, and the whole was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate as an eluent, to afford 17.00 g of the title compound as colorless crystals, melting at 92°-94° C.

後処理

  1. stirringthe whole was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel using a 1:1
  7. additionby volume mixture of hexane and ethyl acetate as an eluent

出典と根拠

ORDレコード
ord-e3e33179047c45a592d53de6df46caae
出典データセット
uspto-grants-1993_09
特許番号
US05242914

関連ノート

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