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

HRID 1252831Notes

Reaction equation

HRID 1252831 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-prolineYield 60.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

2.1 g of the product of Step (c) 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

Sources & evidence

ORD record
ord-393e94c6d2434e588ef76791f3a1ae6c
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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