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

HRID 1704790Notes

Reaction equation

HRID 1704790 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 thirty 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. waitAfter thirty minutes
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is dried
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-ac1f13b559a64345bc0a7c7829b12aa6
Source dataset
uspto-grants-1978_11
Patent number
US04127729

Reaction notes

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