Chloroacetic Acid → HCID 12876168, compound

HRID 127295

Reaction equation

HRID 127295 reaction equation
[SH:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][SH:8])=[O:4].Cl[CH2:15][C:16]([OH:18])=[O:17].[I-].[K+].Cl.[Cl-].[Na+]>C(=O)([O-])[O-].[K+].[K+]>[C:16]([CH2:15][S:8][CH2:7][C@@H:6]([C:9]([OH:11])=[O:10])[NH:5][C:3](=[O:4])[C:2]([S:1][CH2:6][C:9]([OH:11])=[O:10])([CH3:13])[CH3:12])([OH:18])=[O:17]

Participants

7

Reactant 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 656604Bucillamine

Product 1

HCID 12876168HCID 12876168, compoundYield 194.5%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

N-(2-Mercapto-2-methylpropanoyl)-L-cysteine (11.2 g, 0.05 mol) is dissolved in 1 M potassium carbonate and monochloroacetic acid (11.3 g, 0.12 mol) and potassium iodide (1.0 g) are added. The mixture is stirred overnight at room temperature under a nitrogen atmosphere and acidified with 6 N hydrochloric acid. Sodium chloride is added and the mixture is extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution, dried and concentrated to dryness to yield 16.5 g (97.2%) of S-carboxymethyl-N-(2-carboxymethylthio-2-methylpropanoyl)-L-cysteine.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-44272a91e41947378530daad8def6fc9
Source dataset
uspto-grants-1981_03
Patent number
US04255446

Linked notes

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