HCID 12813362, compound → HCID 12813363, compound

HRID 262546Notes

Reaction equation

HRID 262546 reaction equation
C([S:9][CH:10]([CH3:21])[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])(=O)C1C=CC=CC=1>O.[OH-].[NH4+]>[SH:9][CH:10]([CH3:21])[C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12]

Participants

4

Reactant 1

HCID 12813362HCID 12813362, compound

Product 1

HCID 12813363HCID 12813363, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

1-(2-Benzoylthiopropanoyl)-L-proline (5.7 g.) is dissolved in a mixture of water (12 ml.) and concentrated ammonium hydroxide (9 ml.) with stirring. After one hour, the mixture is diluted with water (10 ml.) and filtered. The filtrate is extracted twice with ethyl acetate, concentrated to one-third of the original volume, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride, dried and concentrated to dryness in vacuo. The residue, 1-(2-mercaptopropanoyl)-L-proline, is crystallized from ethyl acetate-hexane, yield 3 g., m.p. (105) 116°-120°.

Workup

  1. filtrationfiltered
  2. extractionThe filtrate is extracted twice with ethyl acetate
  3. concentrationconcentrated to one-third of the original volume
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with saturated sodium chloride
  6. customdried
  7. concentrationconcentrated to dryness in vacuo
  8. customThe residue, 1-(2-mercaptopropanoyl)-L-proline, is crystallized from ethyl acetate-hexane, yield 3 g
  9. custom(105) 116°-120°

Sources & evidence

ORD record
ord-44641933eb87489b81d452b7d1895342
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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