Water → N-(1-Carboxyethyl)-L-cysteine

HRID 433840Notes

Reaction equation

HRID 433840 reaction equation
[C:1]([C:4]1([CH3:12])[NH:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][S:5]1)([OH:3])=[O:2].[OH2:13]>Cl>[C:1]([CH:4]([NH:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][SH:5])[CH3:12])([OH:3])=[O:2].[C:1]([OH:3])(=[O:2])[CH:4]([CH3:12])[OH:13].[NH2:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][SH:5]

Participants

6

Reactant 2

HCID 962WaterHCID 983422-Methyl-2,4-thiazolidinedicarboxylic acid

Product 3

HCID 612Lactic AcidYield 19%HCID 5862L-(+)-CysteineYield 15%HCID 20610684N-(1-Carboxyethyl)-L-cysteineYield 66%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In the electrolysis apparatus of Example 10, a solution of 130.0 g of 2,4-dicarboxy-2-methylthiazolidine in a mixture of 526 ml of water and 144 g of hydrochloric acid was reduced at 9.5 A and temperatures of 16-20° C. After a reaction time of 5 hours, 66% N-(1-carboxyethyl)cysteine, 19% lactic acid and 15% cysteine were obtained. The reaction solution was evaporated, and the solid was recrystallized from 0.5 m hydrochloric acid with exclusion of oxygen. N-(1-Carboxyethyl)cysteine was obtained in colorless crystals.

Workup

  1. customwas reduced at 9.5 A and temperatures of 16-20° C

Sources & evidence

ORD record
ord-1adeb655f6a24e8ea69f4e6bece355bf
Source dataset
uspto-grants-2003_12
Patent number
US06669828B2

Reaction notes

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