Sodium Chloride → t-Butoxycarbonyl-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine

HRID 5082

반응식

HRID 5082 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:32][CH3:33])=[O:31])=[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][CH: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][CH:21]1[C:30]([O:32][CH3:33])=[O:31])=[O:19])([CH3:16])([CH3:15])[CH3:14]

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

생성물 1

HCID 54564631t-Butoxycarbonyl-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

1.11 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added, whilst ice-cooling, to a solution of 3.51 ml of 4-methoxybenzyl mercaptan dissolved in 60 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, a solution of 8.13 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine [prepared as described in step (7) above] in 20 ml of dry dimethylformamide was added dropwise to the mixture, which was then stirred at room temperature for 15 minutes and then at 40° C. for 4 hours. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with water, dried and freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 15:1 by volume mixture of benzene and ethyl acetate), to afford 6.89 g of the title compound as an oil.

후처리

  1. stirringwas then stirred at room temperature for 15 minutes
  2. waitat 40° C. for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationfreed from the solvent by distillation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel (
  8. washeluted with a 15:1 by volume mixture of benzene and ethyl acetate),

출처 및 근거

ORD 기록
ord-2c2ec0e62c9945a7ac22809a68962be3
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

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