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

HRID 5082
Notes
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Reaction equation

HRID 5082 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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),

Sources & evidence

ORD record
ord-2c2ec0e62c9945a7ac22809a68962be3
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05242914

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes