Lithium Hydroxide → HCID 53747184, compound

Participants

Reaction Steps

The operation is carried out in a fashion similar to that described in Example 39, but starting from 2.4 g of ethyl (2R,4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenoxyacetate and 0.2 g of lithium hydroxide. The crude product is purified by chromatography on silica [eluent: ethyl acetate]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. After vigorous stirring in diisopropyl ether, 1.3 g of (2R,4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenoxyacetic acid are thus obtained in the form of an amorphous solid ([α]D20 =+63.7°±1.2° (C=0.96%; CHCl3)) [proton NMR (200 MHz, DMSO D6, δ in ppm), 2 rotamers at room temperature, peak coalescence at 120° C., characteristic chemical shifts at 120° C.: 4.5 (bs, 2H, OCH2CO2); 6.5 (ddd, 1H, N--C6H4 --C in position 4); 6.9 (d, 1H aromatic); 7.1 to 7.7 (m, 7H, aromatic). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 2975, 2930, 2630, 2550, 1735, 1640, 1600, 1555, 1490, 1370, 1240, 1150, 770, 730, 695].

Provenance & Evidence