Hydrochloric Acid → N-Acetyl-S-methyl-L-cysteine

HRID 325331

Reaction equation

HRID 325331 reaction equation
[CH3:1][S:2][CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5].[C:9](OC(=O)C)(=[O:11])[CH3:10].Cl>[OH-].[Na+]>[CH3:1][S:2][CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH:5][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24417(-)-S-Methyl-L-cysteine

Product 1

HCID 13893975N-Acetyl-S-methyl-L-cysteineYield 89.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 13.5 g (100 mmole) of S-methyl-L-cysteine dissolved in 210 ml of 1 N sodium hydroxide solution was ice cooled and 10.4 ml (110 mmole) of acetic anhydride was added thereto dropwise. After 2.0 hours at room temperature, the mixture was acidified to pH 1.0 with 6 N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo to give 15.9 g (89.6% yield) of S-methyl-N-acetyl-L-cysteine as an oil.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1289b227d0be43a18e1a3d5cb961e5a3
Source dataset
uspto-grants-1984_04
Patent number
US04440788

Linked notes

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