Dimethylformamide → (4S)-1-t-Butoxycarbonyl-4-phenylthio-N-t-butyl-L-prolinamide

HRID 1780277Notes

Reaction equation

HRID 1780277 reaction equation
[C:1]1([S-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[C:9]([O:13][C:14]([N:16]1[CH2:27][C@H:26](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][C@H:17]1[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])([CH3:12])([CH3:11])[CH3:10].CN(C)C=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:27][C@@H:26]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:25][C@H:17]1[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 4110039Sodium benzenethiolateHCID 86750836(4R)-1-t-butoxycarbonyl-4-(p-toluenesulfonyloxy)-N-t-butyl-L-prolinamide

Product 1

HCID 57060493(4S)-1-t-Butoxycarbonyl-4-phenylthio-N-t-butyl-L-prolinamideYield 85.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.45 g (3.41 mmol) of sodium thiophenolate was added to a solution of 1.23 g (3.08 mmol) of (4R)-1-t-butoxycarbonyl-4-(p-toluenesulfonyloxy)-N-t-butyl-L-prolinamide [prepared as described in Preparation 6(a)] in 10 ml of a 2:1 by volume mixture of dimethylformamide and ethyl acetate, and the mixture was stirred for 3 hours. At the end of this time, the reaction mixture was poured into a 10% w/v aqueous solution of sodium hydrogen-carbonate and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was purified by preparative thin layer chromatography, using a 1:3 by volume mixture of ethyl acetate and hexane as the developing solvent, to give 1.0 g of the title compound as a colorless powder, melting at 119°-121° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by preparative thin layer chromatography
  6. additionby volume mixture of ethyl acetate and hexane as the developing solvent

Sources & evidence

ORD record
ord-4c9650e99d1c4028a70e8bdb0dbb246a
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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