Glyoxylic Acid → HCID 86680931, compound

HRID 1503177Notes

Reaction equation

HRID 1503177 reaction equation
[S:1]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[NH:3][CH:2]1[C:9]([OH:11])=O.N[C@H:13](C(O)=O)CS.C(O)(=O)C=O.S(Cl)([Cl:26])=O.[CH3:28][OH:29]>>[ClH:26].[CH3:28][O:29][C:9]([CH:2]1[NH:3][CH:4]([C:6]([O:8][CH3:13])=[O:7])[CH2:5][S:1]1)=[O:11]

Participants

6

Reactant 5

HCID 760Glyoxylic AcidHCID 887MethanolHCID 5862L-(+)-CysteineHCID 24386Thionyl ChlorideHCID 72150Tidiacic

Product 1

HCID 86680931HCID 86680931, compoundYield 94%

Procedure

Thiazolidine-2,4-dicarboxylic acid (1.00 g, 5.67 mmol) synthesized from L-cysteine and glyoxylic acid (aqueous solution) were added to a methanol solution (15 ml) of thionyl chloride (22.6 mmol), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated, and to the residue was added ether. The crystals were collected by filtration, washed with ether, and dried under reduced pressure to give thiazolidine-2,4-dicarboxylic acid 2,4-dimethyl ester hydrochloride as crystals (1.29 g, 94.0%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionto the residue was added ether
  3. filtrationThe crystals were collected by filtration
  4. washwashed with ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-81f6adf7ed254f95881f9fe114afebb9
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Reaction notes

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