Toluene → HCID 58979698, compound

Participants

Reaction Conditions

Reaction Steps

1.7 g (9.9 mmol) of (2S)-2-isocyanatohexanoate and 2.0 g (9.1 mmol) of 1-(1,3-benzothiazol-2-yl)cyclopentanol were dissolved in 5 mL of dry toluene and heated at 80° C. for 4 d. After removal of solvent, purification by silica gel column chromatography eluting with hexane:ethyl acetate (2:1) gave 3.5 g of methyl(2S)-2-[({[1-(1,3-benzothiazol-2-yl)cyclopentyl]oxy}carbonyl)amino]hexanoate as a yellow liquid, quantitatively. 1H NMR (300 MHz, CDCl3) δ 8.02 (d, J=8 Hz, 1H), 7.86 (d, J=8 Hz, 1H), 7.47 (t, J=8 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 5.42 (d J=8 Hz, 1H), 4.30 (m, 1H), 3.76 (s, 3H), 2.50 (m, 2H), 1.67-2.08 (m, 6H), 1.30 (m, 6H), 0.92 (t, J=8 Hz, 3H).

Provenance & Evidence