Benzyl 3-aminopropanoate → benzyl N-(E)-[1-oxo-2-(pivaloylthiomethyl)-3-phenylpropenyl]-beta-alaninate

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Reaction Steps

The (E)-2-pivaloylthiomethyl-3-phenylpropenoic acid above is coupled with benzyl β-alaninate according to the experimental procedure described in Example 1 (step D). Yield: 63% (after flash chromatography, eluent: ether/petroleum ether 55/45) oil IR: 3320, 1725, 1650, 1620 cm-1 1H NMR (CDCl3): 7.30 (s, 5H); 7.20 (s, 5H); 6.75 (s, 1H); 4.90 (s, 2H); 3.80 (s, 2H); 3.45 (q app; 2H, J=6.0 Hz); 2.40 (t, 2H, J=6.5 Hz); 1.20 (s, 9H). Microanalysis: C25H29NO4S Calc. % C=68.31 H=6.65 N=3.19 Found. % C=68.02 H=6.73 N=3.01

Provenance & Evidence