Sodium Methoxide → N-[3-mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-cysteine

HRID 372386Notes

Reaction equation

HRID 372386 reaction equation
C([S:4][CH2:5][CH:6]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][S:12]C(=O)NCC)=[O:8])(=O)C.C[O-].[Na+]>CO.Cl>[SH:4][CH2:5][CH:6]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][SH:12])=[O:8]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 57011645N-[3-(acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-S-(N-ethylcarbamoyl)-L-cysteine

Product 1

HCID 54045483N-[3-mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-cysteine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of N-[3-(acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-S-(N-ethylcarbamoyl)-L-cysteine (1.9 g.) in methanol (10 ml.), sodium methoxide (0.84 g.) is added. After 30 minutes, the solution is diluted with 0.1 N hydrochloric acid and extracted with ethyl acetate. The organic layer is dried and concentrated to dryness in vacuo to yield N-[3-mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-cysteine.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer is dried
  3. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-8543faeb0039422cab2ecc0531a8948b
Source dataset
uspto-grants-1978_05
Patent number
US04091024

Reaction notes

Loading…