반응 #73645

반응 방정식

α-ethylbenzylamine

2-benzoylamino-4-methylthiazole-5-carboxylic acid

4-methylmorpholine

iso-butylchloroformate

→

title compound

수율 19.0%

2-Benzoylamino-4-methylthiazole-5-carboxylic Acid (1-Phenylpropyl)amide

수율 19.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction mixture was kept stirring at ambient temperature overnight
3. 3
   농축concentrated
4. 4
   기타Purification of the residue by column chromatography

실험 절차

To a solution of 2-benzoylamino-4-methylthiazole-5-carboxylic acid (0.13 g, 0.50 mmol) and 4-methylmorpholine (0.08 mL, 0.70 mmol) in tetrahydrofuran (20 mL) at 0° C. was added iso-butylchloroformate (0.08 mL, 0.60 mmol). The reaction mixture was stirred for 15 minutes, then warmed to ambient temperature and stirred for another hour before α-ethylbenzylamine (0.1 mL, 0.70 mmol) was added. The reaction mixture was kept stirring at ambient temperature overnight and then concentrated. Purification of the residue by column chromatography afforded the title compound in 19% yield (0.037 g); m. p. 87-89° C.; 1H NMR (CDCl3, 300 MHz) δ 7.89-7.86 (m, 2H), 7.61-7.22 (m, 8H), 5.91 (d, J=7.5 Hz, 1H), 5.02-4.94 (m, 1H), 2.33 (s, 3H), 2.27-1.78 (m, 2H), 0.92 (t, J=7.5 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 165.1, 161.4, 157.0, 152.1, 141.8, 133.3, 131.4, 129.1, 128.7, 127.6, 127.5, 126.6, 118.8, 55.6, 29.3, 16.7, 10.8. MS (ES+) m/z 380.5 (M+1).

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