Triethylamine → HCID 86751852, compound

Participants

Reaction Steps

To a suspension of (±)-vinylphenylalanine (560 mg. 2.9 mmol), NEt3 (1.6 mL, 12 mmol) and 4-dimethylaminopyridine (71 mg, 0.59 mmol) in dry DMSO (3 mL) at 10° C. was added benzyl chloroformate (1.9 mL, 13 mmol), dropwise and with stirring. After being stirred for 1.5 h at 50° C., the reaction mixture was diluted with EtOAc (150 mL) and extracted with NaHCO3 (aq, 50 mL). The organic layer was further extracted with 1N HCl (50 mL) and brine (50 mL). After drying (MgSO4), the volatiles were evaporated in vacuo and the residue purified by flash SiO2 chromatography (10% Et2O-hexane) to give 19 (1.0 g, 82%) as a white solid: mp 68°-70° C.; 1H NMR (500 MHz, CDCl3) δ 3.33 (d, J=13 Hz, 1 H); 3.62 (d, J=13 Hz, 1 H); 5.10-5.25 (m, 4 H); 5.27 (d, J=10 Hz, 1 H); 5.28 (d, J=17 Hz, 1 H); 5.68 (s, 1 H); 6.08 (dd, J=10, 17 Hz, 1 H); 6.90-6.91 (m, 2 H); 7.10-7.20 (m, 3 H); 7.26-7.43 (m, 10 H); 13C NMR (125 MHz, CDCl3) δ 40.4, 65.1, 66.5, 67.8, 116.2, 126.9, 128.1, 128.20, 128.23, 128.4, 128.5, 128.6, 130.0, 130.3, 135.0, 135.4, 136.6, 136.8, 154.4, 171.2; IR (film)3420-3330, 1723 cm-1 ; HRMS (FAB, 3-NOBA) calcd for C26H25NO4Na (M+Na)+ 438.1681, obsd 438.1685. Anal. Calcd for C26H25 NO4 : C, 75.16; H, 6.07; N, 3.37. Found: C, 74.98; H, 6.22; N, 3.37.

Provenance & Evidence