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

HRID 5100

반응식

HRID 5100 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e3e33179047c45a592d53de6df46caae
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

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