Hydrochloric Acid → N-2-methyl-2-(methylthio)propanoyl-L-cysteine

HRID 127296Notes

Reaction equation

HRID 127296 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[CH3:8][C:9]([S:14][CH3:15])([CH3:13])[C:10](Cl)=[O:11].Cl>C(=O)([O-])[O-].[K+].[K+]>[CH3:8][C:9]([S:14][CH3:15])([CH3:13])[C:10]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5862L-(+)-CysteineHCID 134719922-Methyl-2-(methylthio)propanoyl chloride

Product 1

HCID 53027N-2-methyl-2-(methylthio)propanoyl-L-cysteineYield 89.8%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

L-Cysteine (7.1 g) is dissolved in 88 ml of 2 M potassium carbonate and 7.5 g of 2-methyl-2-(methylthio)propanoyl chloride [b.p. 78° C. (37 mmHg)] is added dropwise while stirring under a nitrogen atmosphere at 0° C. After the addition, the mixture is stirred overnight at room temperature. The mixture is acidified with hydrochloric acid and the obtained crystals are separated by filtration and dried to yield 10.4 g (89.8%) of the titled compound.

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred overnight at room temperature
  3. customthe obtained crystals are separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-1ca328e86dbf4115a5c3fbcde3584ea3
Source dataset
uspto-grants-1981_03
Patent number
US04255446

Reaction notes

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