Methanethiol → alpha-Amino-4-hydroxy-3-[(methylthio)methyl]benzeneacetic acid

HRID 225316Notes

Reaction equation

HRID 225316 reaction equation
[CH3:1][SH:2].[OH-].[Na+].Cl.[NH2:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH2:18]Cl)[CH:12]=1)[C:8]([OH:10])=[O:9]>O>[NH2:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH2:18][S:2][CH3:1])[CH:12]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 14798Sodium HydroxideHCID 70578051(-)-alpha-Amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid hydrochloride

Product 1

HCID 23329760alpha-Amino-4-hydroxy-3-[(methylthio)methyl]benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methanethiol (3 g, 0.04 mmole) in 250 ml of water is added sodium hydroxide (0.04 mole) followed by (-)-α-amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid hydrochloride (5 g, 0.02 mole). The solution obtained is stirred overnight. Removal of the solvent by flash evaporation gives a quantitative yield of the title compound combined with 2 equivalents of sodium chloride.

Workup

  1. customThe solution obtained
  2. customRemoval of the solvent
  3. customby flash evaporation

Sources & evidence

ORD record
ord-6a3f7a8fa969404aab3bb8d5d3b77fb3
Source dataset
uspto-grants-1980_11
Patent number
US04236002

Reaction notes

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