Hydrochloric Acid → HCID 136107974, compound

Participants

Reaction Steps

A solution of diethyl N-[4-(3-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propylamino)-3-methylbenzoyl]-(L)-glutamate (0.70 g, 1.1 mmoles) in 1.0N sodium hydroxide (20 mL) was stirred at 55° C. under nitrogen for 18 hours. The reaction mixture was chilled (ice bath) and adjusted to pH 2.5 by the gradual dropwise addition of 6.0N hydrochloric acid. After stirring cold 2 hours, the resulting precipitate was filtered. An attempted recrystallization of the wet cake from dimethylformamide/water failed, so the solution was spin evaporated to a clear oil. The oil was mixed with pH 2.1 aqueous HCl (20 mL) and sonicated 5 minutes to obtain a cream solid which was filtered and dried to give the product; yield, 0.12 g (24%); mp 181° C. (eff.); 1H-NMR (DMSO-d6) δ 1.58 (m, 2H), 1.8-2.1 (m, 2H), 2.12 (s, 3H), 2.2-2.4 (m, 4H), 3.08 (m, 2H), 4.34 (m, 1H), 5.78 (br s, 2H), 5.94 (br s, 2H), 6.52 (d, Jo=9 Hz, 1H), 7.53 (s overlapped, 1H), 7.57 (d overlapped, Jo=10 Hz, 1H), 8.06 (d, 1H), 10.0 (v br s, 1H), 12.2 (v br s, 2H); uv (0.1N NaOH) 296 nm max (18000), 286 min (17500), 274 max (19900), 247 min (5890), 215 max (21000).

Provenance & Evidence