Water → HCID 57501862, compound

HRID 1245045Notes

Reaction equation

HRID 1245045 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[Na+].[CH2:6]([O:13][C:14]([N:16]1[CH2:20][C@H:19](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:18][C@H:17]1[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>CN(C)C=O>[CH2:6]([O:13][C:14]([N:16]1[CH2:20][C@@H:19]([S:3][C:1](=[O:4])[CH3:2])[CH2:18][C@H:17]1[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:35])[CH3:36])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23700354HCID 23700354, compoundHCID 57501863HCID 57501863, compound

Product 1

HCID 57501862HCID 57501862, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

29.34 g (257 mmol) of sodium thioacetate were added to a solution of 127.17 g (245 mmol) of (2S,4R)-1-benzyloxycarbonyl-2-(t-butyldimethylsilyloxy)methyl-4-(p-toluenesulfonyloxy)pyrrolidine [obtained as described in step (a) above] in 245 ml of dimethylformamide, and the resulting mixture was stirred for 1.5 hours at 60° C. After it was cooled to room temperature, water was added and it was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The resulting residue was purified by chromatography on a silica gel using an 8:1 by volume mixture of hexane and ethyl acetate as the eluant to afford 91.67 g (yield: 88%) of the title compound as an orange oil.

Workup

  1. temperatureAfter it was cooled to room temperature
  2. extractionit was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe resulting residue was purified by chromatography on a silica gel using an 8:1
  8. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-1eaa2e5484dd440e82c9ab1ff104f24a
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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