Reacción #73657

Ecuación de reacción

5-phenylpentanoyl chloride

2-amino-4-methylthiazole-5-carboxylic acid benzylamide

pyridine

→

title compound

Rendimiento 98.2%

N-Benzyl-4-methyl-2-(5-phenylpentanamido)thiazole-5-carboxamide

Rendimiento 98.2%

Disolventes

dichloromethane

dichloromethane

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL)
2. 2
   SecadoThe organic phase was dried over anhydrous sodium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónthe filtrate was concentrate in vacuo
5. 5
   OtroThe residue was purified by column chromatography over silica gel
6. 6
   Lavadoeluting with ethyl acetate/hexanes (1/1)

Procedimiento

To a cooled mixture of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.10 g, 0.40 mmol), pyridine (0.096 g, 1.21 mmol), and dimethylaminopyridine (0.010 mg) in anhydrous tetrahydrofuran (5 mL) was added 5-phenylpentanoyl chloride (0.16 g, 0.81 mmol) in anhydrous dichloromethane (1 mL) dropwise. The reaction mixture was stirred at ambient temperature for 2 hours, then diluted with dichloromethane (10 mL) and washed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrate in vacuo. The residue was purified by column chromatography over silica gel, eluting with ethyl acetate/hexanes (1/1) to afford the title compound as a clear oil (0.16 g, 97%) %); 1H NMR (CDCl3, 300 MHz) δ 11.19 (s, br, 1H), 7.33-7.09 (m, 10H), 6.40 (t, J=4.8 Hz, 1H), 4.58 (d, J=5.8 Hz, 2H), 2.60-2.39 (m, 7H), 1.74-1.56 (m, 4H); MS (ES+) m/z 408.6 (M+1).

Fuente