Water → Procysteine

HRID 2057127Notes

Reaction equation

HRID 2057127 reaction equation
O.[OH-].[Na+].O.Cl.[NH2:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][SH:9].Cl[C:14](OC1C=CC=CC=1)=[O:15]>C1(C)C=CC=CC=1>[O:15]=[C:14]1[NH:6][C@H:7]([C:10]([OH:12])=[O:11])[CH2:8][S:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 23462L-Cysteine hydrochloride monohydrate

Product 1

HCID 72390ProcysteineYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A aqueous solution comprising 0.88 liter of water and 184.0 g of sodium hydroxide was dissolved 175.6 g of L-cysteine monohydrochloride monohydrate under ice-cooling, 0.35 liter of a toluene solution containing 313.2 g of phenyl chloroformate was added to the above solution within a range not exceeding 30° C. After stirring the mixture at room temperature for 2 hours, it was allowed to stand and the liquids were separated. The aqueous layer was washed with 0.35 liter of toluene, the layers were separated, and the aqueous layer was concentrated to give 139.84 g of (4R)-2-oxothiazolidin-4-carboxylic acid as colorless crystal.

Workup

  1. temperaturecooling
  2. additionwas added to the above solution within a range not
  3. customexceeding 30° C
  4. customthe liquids were separated
  5. washThe aqueous layer was washed with 0.35 liter of toluene
  6. customthe layers were separated
  7. concentrationthe aqueous layer was concentrated

Sources & evidence

ORD record
ord-b41db29ab6974852ab39821441df3464
Source dataset
uspto-grants-2008_02
Patent number
US07335778B2

Reaction notes

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