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

HRID 569885Notes

Reaction equation

HRID 569885 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

2.1 g. of the product from Example 81 is dissolved in a mixture of water (35 ml.) and concentrated ammonia (35 ml.) under a blanket of argon. After 20 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 the named product 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. temperaturethe solution is chilled in an ice bath
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is dried
  4. concentrationconcentrated to dryness in vacuo
  5. customto yield 1.1 g
  6. customof the named product that is purified by chromatography on silica gel (benzene:acetic acid 75:25) Rf

Sources & evidence

ORD record
ord-2a46ce3f0cad4e4db4b957278f590a79
Source dataset
uspto-grants-1988_03
Patent number
US04734420

Reaction notes

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