3-(Trifluoromethyl)phenyl isocyanate → Methyl 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)oxazole-2-carboxamido)butanoate

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Reaction Steps

To a solution of methyl 2-(5-(4-aminophenyl)oxazole-2-carboxamido)-3-methylbutanoate (Intermediate 1, 150 mg) in THF (3 ml) was added 1-isocyanato-3-(trifluoromethyl)benzene (132 mg) and the mixture was stirred overnight at RT. The mixture was then concentrated, purified by column chromatography (EtOAc:Pet ether, 2:8) and crystallized in CHCl3/Pet ether to give the title compound. Yield: 210 mg (88%). 1HNMR (DMSO-d6, 300 MHz): δ 9.13 (s, 1H), 9.09 (s, 1H), 8.99 (d, 1H), 8.03 (d, 1H), 7.82 (s, 1H), 7.8 (d, 2H), 7.64 (d, 2H), 7.58 (dd, 1H), 7.55 (dd, 1H), 7.34 (m, 1H), 4.3, (m, 1H), 3.68 (s, 3H), 2.24 (m, 1H), 0.95 (d, 6H); MS (ES+) m/z 505 (M+1).

Provenance & Evidence