Salicylaldehyde → ethyl (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylate

Participants

Reaction Steps

The procedure of M. Schubert (J. Biol. Chem., 114, 341 (1936)) was used to prepare 57 starting from L-cysteine ethyl ester and salicylaldehyde. Purification by silica gel chromatography afforded 57 as a thick oil. TLC (silica gel; 3:1 cyclohexane-EtOAc) showed a mixture of 2 isomers, Rf=0.4, 0.5. IR (film): 3300 (sharp), 3000, 1740, 1430 cm-1. NMR (CCl4): 1.28 (3H, t, J=7); 2.9-3.5 (2H, m); 3.8-4.4 (3H, m); 5.50, 5.80 (1H, 2x broad s); 6.5-7.3 (4H, m).

Provenance & Evidence