Carbonodithioic acid, O-ethyl ester → (-)-alpha-Amino-3-[[(ethoxythioxomethyl)thio]methyl]-4-hydroxybenzeneacetic acid

HRID 2049220Notes

Reaction equation

HRID 2049220 reaction equation
Cl.[NH2:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14]Cl)[CH:8]=1)[C:4]([OH:6])=[O:5].[C:16]([S-:21])(=[S:20])[O:17][CH2:18][CH3:19].[K]>O>[NH2:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][S:21][C:16]([O:17][CH2:18][CH3:19])=[S:20])[CH:8]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 1248527Carbonodithioic acid, O-ethyl esterHCID 5462222PotassiumHCID 70578051(-)-alpha-Amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid hydrochloride

Product 1

HCID 23329752(-)-alpha-Amino-3-[[(ethoxythioxomethyl)thio]methyl]-4-hydroxybenzeneacetic acidYield 58.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (-)-α-amino-3-(chloromethyl)-4-hydroxybenzeneacetic acid hydrochloride (1 g, 0.004 mole) in 20 ml of water is added carbonodithioic acid, O-ethyl ester, potassium salt (1.26 g, 0.08 mole). Within a few minutes a precipitate begins to form. The mixture is stirred at room temperature for 3 hours. The solid precipitate is filtered, washed with water and dried to give 58.3% of the title compound.

Workup

  1. waitWithin a few minutes a precipitate begins
  2. customto form
  3. filtrationThe solid precipitate is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a21b4aff7de4433597c8768fe3637390
Source dataset
uspto-grants-1980_04
Patent number
US04197240

Reaction notes

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