Benzyl 3-aminopropanoate → benzyl N-(Z)-[1-oxo-2-(acetylthiomethyl)-3-(4-methoxyphenyl)propenyl]-beta-alaninate

Participants

Reaction Steps

The (Z)-2-acetylthiomethyl-3-(4-methoxyphenyl)propenoic acid obtained in step C is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 74% (crystallization in a dichloromethane/petroleum ether mixture) m.p. 96° C. IR (nujol): 3280, 1740, 1690, 1640, 1620 cm-1 1H NMR (CDCl3 /TMS): 7.65 (s, 1H): 7.35 to 7.15 (m, 7H); 6.95 to 6.80 (m, 3H); 5.10 (s, 2H); 4.00 (s, 2H); 3.75 (s, 3H); 3.60 (q, 2H, J app.=6 Hz); 2.60 (t, 2H, J=6 Hz); 2.30 (s, 3H). 13C NMR (CDCl3): 196.2; 172.0; 167.1; 159.8; 137.9; 135.6; 130.9; 128.5; 128.2; 128.1; 127.2; 114.1; 66.3; 55.2; 35.6; 33.8; 30.2; 26.6. Microanalysis: C23H25O5NS Calc. % C=64.61 H=5.89 N=3.27 Found. % C=64.20 H=5.73 N=3.48

Provenance & Evidence