Sodium Hydroxide → HCID 9851483, compound

Participants

Reaction Steps

A stirred solution of 1-benzyl-4-(4-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (2.95 g, Reference Example 16) in a mixture of acetonitrile (150 mL) and ethanol (125 mL), at 50° C., was treated slowly with aqueous sodium hydroxide solution (0.46 mL, 30%). After stirring for 8 hours at room temperature and then gentle stirring for a week, the mixture was filtered. The solid was washed with dichloromethane (30 mL), then dried under reduced pressure (2.7 kPa) and then treated with water (200 mL). The mixture was acidified by addition of hydrochloric acid (3.5 mL, 1 M), then allowed to stand at room temperature for 15 hours, then treated with ethyl acetate (400 mL) and then filtered to give the title compound (1.16 g) as a white powder, m.p. 255° C. 1H-NMR [400 MHz, (CD3)2SO]: δ 2.27 (s, 3H); 2.45 to 2.60 (m, 1H); 2.80 to 3.00 (m, 4H); 3.49 (m, 1H); 3.57 (s, 2H); 3.58 and 3.68 (2 d, J=14 Hz, 2H); 3.90 (s, 3H); 6.85 (bd, J=8 Hz, 1H); 6.95 (bt, J=7 Hz, 1H); 7.02 (bs, 1H); 7.05 to 7.20 (m, 2H); 7.20 to 7.30 (m, 3H); 7.30 to 7.40 (m, 4H); 7.52 (bd, J=8 Hz, 2H); 7.82 (bd, J=8 Hz, 1H); 8.04 (d, J=8 Hz, 1H); 8.48 (bs, 1H); 8.59 (bs, 1H); 10.07 (bs, 1H). MS(LSIMS): 593[M+HI]+.

Provenance & Evidence