2-Amino-2-thioxoethyl 2,2-dimethylpropanoate → Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoate

Participants

Reaction Conditions

Reaction Steps

A sample of rac-3-(2-bromo-pentanoyl)-benzoic acid methyl ester (0.60 g) and and 2-(tert.-butylcarbonyloxy)thioacetamide (0.36 g) in EtOH (4 mL) was heated at reflux for 5 h. The mixture was partitioned between AcOEt and 5% NaHCO3 solution, the organic layer was washed with brine, dried and evaporated. A solution of the residual oil and of NaOMe (0.13 g) in MeOH (10 mL) was stirred at 60° C. for 30 min. The solution was diluted with AcOEt, washed with 1N HCl and brine, dried and evaporated to give 3-(2-hydroxymethyl-5-methyl-thiazol-4-yl)-benzoic acid methyl ester (0.44 g) as an oil.

Provenance & Evidence