Methanol → AG-G-95136

HRID 1181637Notes

Reaction equation

HRID 1181637 reaction equation
C1(C2[S:8][CH2:9][CH:10]([C:12](O)=O)[N:11]=2)C=CC=CC=1.CI.[CH:17]([N-]C(C)C)(C)C.[Li+].[OH-:25].[Li+].[CH3:27][OH:28]>Cl[Ti](Cl)(Cl)Cl>[CH3:17][O:25][C:27](=[O:28])[C@@:10]([CH3:12])([CH2:9][SH:8])[NH2:11]

Participants

7

Reactant 5

HCID 887MethanolHCID 3939Lithium HydroxideHCID 6328Methyl iodideHCID 883272-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid2×HCID 2724682Lithium diisopropylamide

Product 1

HCID 11095302AG-G-95136

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

(S)-Cysteine is reacted with benzoic acid to form 2-phenylthiazoline-4-carboxylic acid. 2-Phenylthiazoline-4-carboxylic acid is amidated with 4-benzyloxazolidone. The amidated 2-phenylthiazoline-4-carboxylic acid is alkylated with methyl iodide in the presence of TiCl4 and lithium diisopropylamide. The alkylated species is hydrolyzed by lithium hydroxide in methanol to obtain (S)-2-methylcysteine methyl ester.

Sources & evidence

ORD record
ord-844ad61a228144f88bc6575ce68aa304
Source dataset
uspto-grants-2007_10
Patent number
US07285676B2

Reaction notes

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