1-Bromo-5-isocyanatopentane → 1-(5-Bromopent-1-yl)-5-(3,4-difluorobenzyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone

Participants

Reaction Steps

To 2-amino-4-(3,4-difluorophenyl)-3-oxobutyric acid methyl ester (0.100 g, 0.344 mmol) in 2 mL water was added 1-bromo-5-isocyanatopentane (0.3 mL), and the reaction mixture refluxed for 3 hours. The reaction mixture was concentrated and partitioned between EtOAc (30 mL) and 1N HCl (10 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over sodium sulfate, filtered and concentrated to give 0.080 g (55%) of the product as a syrup; 1H-NMR (CDCl3) δ1.36-1.81 (m, 6 H), 3.34 (t, J=6.6 Hz, 2 H), 3.32-3.37 (m, 2 H), 3.86 (s, 3 H), 4.21 (s, 2 H), 6.91-7.16 (m, 3 H), 9.53 (s, 1 H).

Provenance & Evidence