1-(3-Acetylthiopropanoyl)-L-proline → 1-(3-Mercapto-1-oxopropyl)-L-proline

HRID 262551Notes

Reaction equation

HRID 262551 reaction equation
C([S:4][CH2:5][CH2:6][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>N>[SH:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8]

Participants

3

Reactant 1

HCID 132083011-(3-Acetylthiopropanoyl)-L-proline

Product 1

HCID 999781-(3-Mercapto-1-oxopropyl)-L-proline

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

1-(3-Acetylthiopropanoyl)-L-proline (0.8 g.) is dissolved in 5.5 N methanolic ammonia (5 ml.) and the solution kept under argon at room temperature. After 2 hours the solvent is removed in vacuo, the residue is dissolved in water and applied to an ion exchange column on the H+ cycle [Dowex 50(Analytical grade)] and eluted with water. The fractions that give thiol positive reaction are pooled and concentrated to dryness, yield 0.6 g. This product is crystallized from ethyl acetate-hexane as in Procedure A to obtain 1-(3-mercaptopropanoyl)-L-proline.

Workup

  1. customkept under argon at room temperature
  2. customAfter 2 hours the solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in water
  4. washeluted with water
  5. customThe fractions that give
  6. concentrationconcentrated to dryness, yield 0.6 g
  7. customThis product is crystallized from ethyl acetate-hexane as in Procedure A

Sources & evidence

ORD record
ord-d5669086b9b64269a14edb699e6c9aa2
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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