تفاعل #73657

معادلة التفاعل

5-phenylpentanoyl chloride

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

pyridine

→

title compound

المردود 98.2%

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

المردود 98.2%

المذيبات

dichloromethane

dichloromethane

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL)
2. 2
   تجفيفThe organic phase was dried over anhydrous sodium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزthe filtrate was concentrate in vacuo
5. 5
   أخرىThe residue was purified by column chromatography over silica gel
6. 6
   غسيلeluting with ethyl acetate/hexanes (1/1)

الإجراء التجريبي

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).

المصدر