Sodium Hydroxide → HCID 9935773, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl (R/S) 3-(1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-2,3-dihydro-1H-indol-5-yl)-butyrate [2.8 g, Reference Example 4(a)] in methanol (about 150 ml) was treated with aqueous sodium hydroxide solution (15 ml, 1M). The mixture was warmed at about 50° C. for 3 hours, then treated with a further aliquot of aqueous sodium hydroxide solution (7.5 ml). After a further 2-3 hours at 50° C. TLC analysis indicated complete reaction. The bulk of the methanol was removed by evaporation and the residue was diluted with hydrochloric acid (about 200 ml, 1M). The resulting mixture was stirred for about 30 minutes, then the solid was collected by filtration, washed with water, and dried to give the title compound (2.3 g) as a very light orange powder. LC-MS: RT=3.84 minutes (100% total area by ELS); MS (ES+) 502 (MH+), 524 (MNa+).

Provenance & Evidence