Sodium Methoxide → Nalpha-[3-Mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-arginine

HRID 262375Notes

Reaction equation

HRID 262375 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][CH2:12][CH2:13][NH:14][C:15](=[NH:17])[NH2:16])=[O:8])(=O)C.C[O-].[Na+]>CO>[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][CH2:12][CH2:13][NH:14][C:15](=[NH:16])[NH2:17])=[O:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178500599HCID 178500599, compound

Product 1

HCID 178500645Nalpha-[3-Mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-arginine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Nα -[3-(acetylthio)-2-(methoxycarbonylmethyl)propanoyl]-L-arginine (1.9 g.) in methanol (10 ml.), sodium methoxide (0.56 g.) is added. After ten minutes, the solution is applied to a column of Dowex 50 resin and the column is washed with water until no more acidic material is eluted. Nα -[3-mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-arginine is then eluted with a pyridine-acetate buffer of pH 6.5.

Workup

  1. waitAfter ten minutes
  2. washthe column is washed with water until no more acidic material
  3. washis eluted
  4. washNα -[3-mercapto-2-(methoxycarbonylmethyl)propanoyl]-L-arginine is then eluted with a pyridine-acetate buffer of pH 6.5

Sources & evidence

ORD record
ord-5b4d11319f244af3884b9b2f5a8ab0e0
Source dataset
uspto-grants-1979_05
Patent number
US04154736

Reaction notes

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