L-(+)-Cysteine → HCID 57312911, compound

HRID 1503175Notes

Reaction equation

HRID 1503175 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[C:8]([O:12][CH2:13][CH3:14])(=[O:11])[CH:9]=O>O>[CH3:14][CH2:13][O:12][C:8]([CH:9]1[NH:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]1)=[O:11]

Participants

4

Reactant 2

HCID 5862L-(+)-CysteineHCID 70211Ethyl oxoacetate

Product 1

HCID 57312911HCID 57312911, compoundYield 29,313.199%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-Cysteine (60.4 g, 0.50 mmol) and ethyl glyoxylate (polymer, 47% toluene solution, 50.9 g, 0.234 mol) were added to water (150 ml), and the mixture was stirred at room temperature for 50 hours. The obtained solution was concentrated under reduced pressure, and the precipitated solid was collected by filtration. The obtained white solid (about 40 g) was suspended in water (100 ml), and the suspension was stirred for 16 hours at slurry state. The white crystals were collected by filtration, and dried under reduced pressure to give thiazolidine-2,4-dicarboxylic acid 2-ethyl ester as a white solid (30.08 g).

Workup

  1. concentrationThe obtained solution was concentrated under reduced pressure
  2. filtrationthe precipitated solid was collected by filtration
  3. stirringthe suspension was stirred for 16 hours at slurry state
  4. filtrationThe white crystals were collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-12434506e2874cdbb5e2421ef6840927
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Reaction notes

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