Benzoic Acid → 2-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

HRID 1181636Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[C:8](O)(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:9]1([C:8]2[S:4][CH2:3][CH:2]([C:5]([OH:7])=[O:6])[N:1]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 243Benzoic Acid

HCID 92851D-Cysteine

Product 1

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

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-3718023934174bdd9b598475fd833890
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285676B2

Reaction notes

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