Chloroacetonitrile → HCID 72700447, compound

Participants

Reaction Steps

Chloroacetonitrile (5 mL) and DIPEA (160 mg, 0.21 mL, 1.2 mmol) were added to Boc-Leu-OH (252 mg, 1.09 mmol) and stirred for 12 h. The solvent was removed under reduced pressure and SiO2 flash chromatography (20% ethyl acetate in hexanes) afforded 284 mg of a pale yellow oil in 96% yield. Rf 0.5 in 20% ethyl acetate in hexanes. 1H NMR (500 MHz, CDCl3): δ 5.00 (d, J=7.7 Hz, 1H), 4.80-4.65 (m, 2H), 4.30-4.29 (m, 1H), 1.70-1.65 (m, 1H), 1.60-1.47 (m, 2H), 1.39 (s, 9H), 0.91-0.89 (m, 6H); 13C NMR (125 MHz, CDCl3): δ 172.2, 155.5, 114.21, 80.3, 53.2, 52.0, 41.0, 28.3, 24.8, 22.8, 21.7; HRMS (ESI) m/z calcd for C13H22N2O4Na [M+Na]+ 293.147. found 293.151.

Provenance & Evidence