Hydrochloric Acid → 1-[3-Mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-proline

HRID 1704784Notes

Reaction equation

HRID 1704784 reaction equation
C([S:4][CH2:5][CH:6]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[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.Cl.[Cl-].[Na+]>O.N>[SH:4][CH2:5][CH:6]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 541123831-[3-(Acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-L-proline

Product 1

HCID 539411441-[3-Mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

1-[3-(Acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-L-proline (2.1 g.) is dissolved in a mixture of water (35 ml.) and concentrated ammonia (35 ml.) under a blanket of argon. After twenty minutes, the solution is chilled in an ice bath, made acidic with concentrated hydrochloric acid, saturated with sodium chloride and extracted with ethyl acetate. The organic layer is dried and concentrated to dryness in vacuo to yield 1.1 g. of 1-[3-mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-proline that is purified by chromatography on silica gel (benzene:acetic acid 75:25). Rf : 0.35 (silica gel, benzene:acetic acid, 75:25).

Workup

  1. waitAfter twenty minutes
  2. temperaturethe solution is chilled in an ice bath
  3. extractionextracted with ethyl acetate
  4. customThe organic layer is dried
  5. concentrationconcentrated to dryness in vacuo
  6. customto yield 1.1 g
  7. customof 1-[3-mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-proline that is purified by chromatography on silica gel (benzene:acetic acid 75:25)

Sources & evidence

ORD record
ord-8865a95d93e847c180e8b9b73b84b412
Source dataset
uspto-grants-1978_11
Patent number
US04127729

Reaction notes

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