Hydrochloric Acid → HCID 70153857, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-3-benzoylamino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenyl-acetylamino}phenyl)-propanoic acid methyl ester [4.08 g, Reference Example 12(a)], and methanol (40 ml) was heated to 40° C. and then treated with 10% aqueous sodium hydroxide solution (34 ml). After stirring at 40° C. for 2.5 hours, the reaction mixture was cooled and then acidified to pH 1.0 by addition of hydrochloric acid (1M). The resultant white solid was collected, washed with water and then dried in vacuo. Recrystallisation from acetic acid gave the title compound as a white crystalline solid (3.2 g), m.p. 220-222° C. MS: MH+ 581. [Elemental analysis:—C, 68.0; H, 5.4; N, 9.5%. Calculated for C33H32N4O6:—C, 68.3; H, 5.6; N, 9.65%]. 99% ee by HPLC analysis on a CHIRALPAK AD F294 column eluting with heptane:isopropanol:ethanol:trifluoroacetic acid (200:25:25:1) at a rate of 0.7 ml/min.

Provenance & Evidence