1-[3-acetylthio-2-(methylthiomethyl)propanoyl]-L-proline → [3-mercapto-2-(methylthiomethyl)propanoyl]-L-proline

HRID 47133Notes

Reaction equation

HRID 47133 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:17][S:18]C)[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:18][CH2:17][CH:6]([CH2:5][S:4][CH3:1])[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 539119981-[3-acetylthio-2-(methylthiomethyl)propanoyl]-L-proline

Product 1

HCID 53870807[3-mercapto-2-(methylthiomethyl)propanoyl]-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

1-[3-(acetylthio)-2-(methylthiomethyl)propanoyl]-L-proline (1.2 g.) is dissolved in a mixture of water (12 ml.) and concentrated ammonia (12 ml.) under a blanket of argon. After twenty minutes, the reaction mixture is acidified and extracted with ethyl acetate. The organic layer is dried and concentrated to dryness to yield 1-([3-mercapto-2-(methylthiomethyl)propanoyl]-L-proline.

Workup

  1. waitAfter twenty minutes
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is dried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cd8b2e9eff664f34b0beda48172fe3a2
Source dataset
uspto-grants-1979_11
Patent number
US04176235

Reaction notes

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