N-(3-benzoylthiopropanoyl)-L-alanine → N-(3-Sulfanylpropanoyl)-L-alanine

HRID 1252815Notes

Reaction equation

HRID 1252815 reaction equation
C([S:9][CH2:10][CH2:11][C:12]([NH:14][C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])=[O:13])(=O)C1C=CC=CC=1>O.[OH-].[NH4+]>[SH:9][CH2:10][CH2:11][C:12]([NH:14][C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 13036931N-(3-benzoylthiopropanoyl)-L-alanine

Product 1

HCID 13036940N-(3-Sulfanylpropanoyl)-L-alanineYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

N-(3-benzoylthiopropanoyl)-L-alanine (4.2 g) is dissolved in a mixture of water (7.5 ml) and concentrated ammonium hydroxide (6 ml). After one hour, the mixture is diluted with water, filtered and the filtrate is extracted with ethyl acetate. The aqueous phase is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water, dried and concentrated to dryness in vacuo. The residue is crystallized from ethyl acetate-hexane to yield 1.87 g of N-(3-mercaptopropanoyl)-L-alanine, m.p. 79°-81°.

Workup

  1. filtrationfiltered
  2. extractionthe filtrate is extracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. customdried
  6. concentrationconcentrated to dryness in vacuo
  7. customThe residue is crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9116ed926520467993fe44e21630607f
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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