2-Amino-2-thioxoethyl 2,2-dimethylpropanoate → Methyl 3-[2-hydroxymethyl-5-methyl-thiazol-4-yl]-benzoate
反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH:11](Br)[CH3:12])[CH:5]=1.C(C([O:22][CH2:23][C:24]([NH2:26])=[S:25])=O)(C)(C)C>CCO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:26]=[C:24]([CH2:23][OH:22])[S:25][C:11]=2[CH3:12])[CH:5]=1参加物
4
反応条件
- 温度
- 60 °C
実験手順
A solution of rac-3-(2-bromo-propionyl)-benzoic acid methyl ester (2.71 g) and 2-(tert.-butylcarbonyloxy)thioacetamide (2.1 g) in EtOH (20 mL) was heated at reflux for 6 h. The mixture was partitioned between AcOEt and brine, and the organic layer was dried and evaporated. A solution of the residual oil and NaOMe (0.54 g) in MeOH (20 mL) was stirred at 60° C. for 1 h. 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 (1.17 g) as white crystals, MS (ISP) 264.1 [(M+H)+].