Succinic anhydride → (4R)-3-(3-Carboxypropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

Beteiligte Stoffe

Reaktionsschritte

To a stirred solution of (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid (4.5 g) and triethylamine (4.0 g) in acetone (100 ml), succinic anhydride (2.0 g) was added at room temperature, and stirred for 3 hours at the same temperature. The reaction mixture was concentrated in vacuo, and acidified with dilute hydrochloric acid. The separated oil was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 4.9 g (75%) of the titled compound: mp 190°-191° C. (dec.) (ethyl acetate-methanol); [α]D27 +181.6° (c=1.0, methanol). IR (nujol, cm-1): 3210 (OH), 1720 (COOH), 1618 (CON), 1602 (aromatic), 1245, 1173, 940, 763. NMR (DMSO-6, δ): 2.0-2.7 (4H, m, --CH2CH2 --), 3.03 (1H, ABq (A part), d, J=11.0, 10.0 Hz, C5 --HA), 3.36 (1H, ABq (B part), d, J=11.0, 7.0 Hz, C5 --HB), 4.61 and 5.07 (1H, dd, J=10.0, 7.0 Hz and m, C4 --H), 6.36 (1H, s, C2 --H), 6.5-8.0 (4H, arom. H). TLC: Rf value* 0.35.

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