Ethanol → (R)-2-Acetamido-3-methoxy-N-(4-(3-methoxypropyl)benzyl)-propanamide

Participants

Reaction Steps

An EtOH solution (30 mL) of (R)-2-acetamido-3-methoxy-N-(4-(3-methoxyprop-1-ynyl)benzyl)propanamide ((R)-6) (1.00 g, 3.1 mmol) was treated with H2 (1 atm) in the presence of 10% PtO2 (50 mg) at room temperature (16 h). The mixture was carefully filtered through a bed of Celite®. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel with EtOAc as the eluant to obtain (R)-7 (510 mg, 51%) as a white solid: Rf=0.27 (EtOAc); mp 105-107° C.; [α]25D +3.0° (c 0.5, DMSO); IR (nujol) 3283, 3085, 1638, 1550, 1457, 1379, 1299, 1122, 979, 725, 605 cm−1; 1H NMR (CDCl3) 1.81-1.92 (m, CH2), 2.03 (s, CH3CO), 2.67 (t, J=7.8 Hz, CH2Ph), 3.33-3.46 (m, CHH′O, CH2O and 2 OCH3), 3.80 (dd, J=4.0, 9.1 Hz, CHH′O), 4.44 (d, J=5.7 Hz, CH2N), 4.50-4.57 (m, CH), 6.45 (br d, J=6.6 Hz, NHC(O)CH3), 6.70-6.75 (br t, CH2NH), 7.15-7.20 (m, 4 ArH); 13C NMR (CDCl3) 23.2 (CH3CO), 31.2, 31.9 (2 CH2), 43.3 (CH2N), 52.4 (CHCH2), 58.6, 59.1 (2 OCH3), 71.7, 71.9 (2 CH2OMe), 127.5, 128.8, 135.3, 141.4 (C6H4), 169.9, 170.2 (2C(O)); HRMS (M+Na+) (ESI+) 317.1784 [M+Na+] (calcd for C17H26N2O4Na+ 345.1790); Anal. Calcd. for C17H26N2O4: C, 63.33; H, 8.13; N, 8.69. Found: C, 63.12; H, 8.13; N, 8.64.

Provenance & Evidence