Methanol → HCID 25227533, compound

Participants

Reaction Steps

To a stirred mixture of 3 (0.4 mmol) in dry CH2Cl2 (2 mL), kept at 0° C. under N2, Et3N (1.59 mmol) and 3-phenylpropionyl chloride (0.6 mmol) were added dropwise. The mixture was reacted at 0° C. for 30 min and at room temperature for 2 h, then concentrated. Purification of the residue by flash-chromatography (cyclohexane/EtOAc 1:1 to 3:7) and recrystallization gave URB783 as a white solid. Yield 60%. Mp 104-106° C. (acetone/petroleum ether). [α]D20=−13° (c 0.5, MeOH). MS (EI): m/z 219 (M+), 91 (100). IR (Nujol) 3333, 1832, 1625, 1541 cm−1; 1H NMR (CDCl3) δ 2.57 (br s, 1H), 2.99 (t, 2H), 4.34 (t, 1H, J=5 Hz), 4.43 (dd, 1H, J1=5 Hz, J2=6.5), 5.14 (m, 1H), 5.96 (br s, 1H), 7.18-7.36 (m, 5H) ppm. 13C NMR (CDCl3): δ 31.2 (CH2), 37.7 (CH2), 58.4 (CH), 66.1 (CH2), 126.5 (CH), 128.3 (2CH), 128.7 (2CH), 140.2, 168.4 (C═O), 172.5 (C═O) ppm.

Provenance & Evidence