Methyl iodide → 4-Thiazolecarboxylic acid, 4,5-dihydro-4-methyl-2-phenyl-

HRID 982888Notes

Reaction equation

HRID 982888 reaction equation
[C:1]1([C:7]2[S:8][CH2:9][CH:10]([C:12]([OH:14])=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15]I>O1CCCC1>[C:1]1([C:7]2[S:8][CH2:9][C:10]([CH3:15])([C:12]([OH:14])=[O:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 883272-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

Product 1

HCID 114814354-Thiazolecarboxylic acid, 4,5-dihydro-4-methyl-2-phenyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cysteine, benzonitrile, and 5 equivalents of triethylamine were refluxed in ethanol for 6-8 hours to obtain a 66-70% yield of 2-phenylthiazoline-4-carboxylic acid. The 2-phenylthiazoline-4 carboxylic acid was reacted with 2.05 equivalents of base and 1 equivalent of methyl iodide in tetrahydrofuran at 0° C. to form 2-phenyl-4-methylthiazoline-4 carboxylic acid. The 2-phenyl-4-methylthiazoline-4 carboxylic acid can be resolved and isolated as the (S)-enantiomer using emulsion crystallization, and subsequently hydrolyzed with hydrochloric acid, thereby obtaining (S)-2-methylcysteine hydrochloride.

Sources & evidence

ORD record
ord-0895dd21a56d48b6a9f53d9da4a0ed21
Source dataset
uspto-grants-2005_03
Patent number
US06861532B2

Reaction notes

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