Chloroacetonitrile → HCID 72700533, compound

Participants

Reaction Steps

Chloroacetonitrile (1 mL) and DIPEA (20 mg, 34 μL, 0.21 mmol) were added to Boc-p-benzoylphenylalanine (61 mg, 0.19 mmol). The reaction was stirred for 18 h, then concentrated under reduced pressure. SiO2 flash chromatography (40% ethyl acetate in hexanes) afforded 70 mg of a pale yellow oil in 93% yield. Rf 0.5 in 50% ethyl acetate in hexanes. 1H NMR (500 MHz, CDCl3) δ 7.79 (dd, J=7.1, 4.9 Hz, 4H), 7.59 (t, J=7.6 Hz, 1H), 7.48 (t, J=7.6 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 5.00 (d, J=7.4 Hz, 1H), 4.83 (d, J=15.7 Hz, 1H), 4.72-4.69 (m, 2H), 3.25 (dd, J=13.7, 5.8 Hz, 1H), 3.16 (dd, J=13.1, 6.5 Hz, 1H), 1.43 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 196.4, 170.6, 155.1, 140.3, 137.6, 136.9, 132.7, 130.8, 130.2, 129.4, 128.5, 113.9; HRMS (ESI) m/z calcd for C23H24N2NaO5 [M+Na]+ 431.158. found 431.158.

Provenance & Evidence