HCID 12813362, compound → HCID 12813363, compound

HRID 2071377Notes

Reaction equation

HRID 2071377 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 1 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-3750686a77d345c7ac32996a269e3d6c
Source dataset
uspto-grants-1977_09
Patent number
US04046889

Reaction notes

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