Sodium Hydroxide → HCID 9873611, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 1-benzoyl-2-(4-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (0.33 g, Reference Example 13) in a mixture of ethanol (4 ml) and acetonitrile (40 ml), at 20° C., was treated dropwise with aqueous sodium hydroxide solution (0. 15 ml, 10 N). After stirring for 6 days the mixture was filtered and the insoluble light brown solid was triturated twice with acetonitrile (5 ml), then twice with dichloromethane (2.5 ml) and then dried. The solid was dissolved in water (30 ml) and filtered. The filtrate was cooled to 5° C. and the pH of the mixture adjusted to 2 by dropwise addition of hydrochloric acid (1.2 ml, 1N). The resulting white precipitate was filtered then washed three times with water (5 ml), then twice with diisopropyl ether (10 ml) and then dried under reduced pressure (40° C. and 2.7 kPa) to afford the title compound (0.134 g) as an off-white powder, m.p. 155° C. (with decomposition). 1H-NMR [500 MHz, (CD3)2SO at 383° K.]: δ 2.15 (m, 2H); 2.27 (s, 3H); 2.96 (m, 1H); 3.59 (s, 2H); 3.75 (m, 2H); 3.89 (s, 3H); 5.32 (m, 1H); 6.87 (bd, J=8 Hz, 1H); 6.98 (t, J=7.5 Hz, 1H); 7.02 (d, J=1.5 Hz, 1H); 7.10 to 7.25 (m, 4H); 7.30 to 7.45 (m, 5H); 7.52 (d, J=8.5 Hz, 2H); 7.67 (d, J=8 Hz, 1H); 7.99 (d, J=8 Hz, 1H); 8.15 (bs, 1H); 8.21 (bs, 1H); 9.55 (bs, 1H). MS(ES): 629 [M+Na]+.

Provenance & Evidence