반응 #73657

반응 방정식

5-phenylpentanoyl chloride

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

pyridine

→

title compound

수율 98.2%

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

수율 98.2%

용매

dichloromethane

dichloromethane

tetrahydrofuran

반응 조건

후처리

1. 1
   세척washed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL)
2. 2
   건조The organic phase was dried over anhydrous sodium sulfate
3. 3
   여과filtered
4. 4
   농축the filtrate was concentrate in vacuo
5. 5
   기타The residue was purified by column chromatography over silica gel
6. 6
   세척eluting with ethyl acetate/hexanes (1/1)

실험 절차

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).

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