1-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline → 1-(3-mercapto-2-trifluoromethylpropanoyl)-L-proline

HRID 1252809Notes

Reaction equation

HRID 1252809 reaction equation
C([S:4][CH2:5][CH:6]([C:17]([F:20])([F:19])[F:18])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=O)C>O.N>[SH:4][CH2:5][CH:6]([C:17]([F:20])([F:18])[F:19])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8]

Participants

4

Reactant 1

HCID 541522191-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline

Product 1

HCID 131927111-(3-mercapto-2-trifluoromethylpropanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

N-(3-Acetylthio-2-trifluoromethylpropanoyl)-L-proline (4 g) is dissolved in a mixture of water (8 ml) and concentrated ammonia (8 ml) under a blanket of nitrogen. After twenty-five minutes stirring at room temperature, the reaction mixture is chilled, acidified and extracted with ethyl acetate. The organic layer is concentrated to dryness in vacuo to yield N-(3-mercapto-2-trifluoromethylpropanoyl)-L-proline.

Workup

  1. temperaturethe reaction mixture is chilled
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer is concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-356efd206147469eb285578b1c293ab7
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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