Sodium Hydroxide → HCID 9959083, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-acetyl-4-(4-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (1.62 g, Reference Example 1) in anhydrous ethanol (60 ml) was treated dropwise with sodium hydroxide solution (48 ml, 0.1 M). After stirring for 15 hours at 23° C. the mixture was evaporated (40° C. and 2.7 kPa). The residue was diluted with distilled water (200 ml), then cooled to 5° C. and then the pH of the mixture was adjusted to 2 by dropwise addition of hydrochloric acid (1N) resulting in the precipitation of a white solid. After stirring at 23° C. for 15 hours the mixture was filtered. The white solid was dried under reduced pressure (2.7 kPa) then triturated with ether affording the title compound (1 g) as a white solid, m.p. 242° C. 1H-NMR [600 MHz, (CD3)2SO]: δ 1.95 and 1.98 (2 s, 3H); 2.25 (s, 3H); 3.10 to 3.95 (m, 6H); 3.58 (s, 2H); 3.89 (s, 3H); 6.85 (bd, J=8 Hz, 1H); 6.95 (t, J=7.5 Hz, 1H); 7.02 (bs, 1H); 7.13 (t, J=7.5 Hz, 1H); 7.17 (d, J=7.5 Hz, 1H); 7.25 and 7.28 (2 d, J=8 Hz, 2H); 7.50 to 7.60 (m, 2H); 7.80 (d, J=7.5 Hz, 1H); 8.04 (d, J=8 Hz, 1H); 8.48 (s, 1H); 8.59 (s, 1H). MS [FAB (meta-nitrobenzylalcohol)]: 545 [M+H]+.

Provenance & Evidence