Ammonia → HCID 15132288, compound

Participants

Reaction Steps

A stream of ammonia is passed for 11 hours at a temperature in the region of 25° C. into a solution of methyl (RS)-3-[3-(3-methylphenyl)ureido]-N-(tertbutoxycarbonylmethyl)-N-phenylsuccinamate (4.7 g) in methanol (150 cc). The solution is then outgassed with a stream of nitrogen and concentrated under vacuum (2.7 kPa) at 60° C. The residue is crystallised in diethyl ether and the solid extracted with dichloromethane (40 cc). The solution thereby obtained is purified by chromatography on silica (0.063-0.200 mm) (25 g) contained in a column 1.6 cm in diameter [eluent: methylene chloride (1100 cc), then methylene chloride/methanol (98.5:1.5 by volume)], collecting 15-cc fractions. Fractions 80 to 127 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. After crystallisation in petroleum ether, (RS)-2-[3-(3-methylphenyl)ureido]-N-(tert-butoxycarbonylmethyl)-N-phenylsuccinamide (1.1 g), m.p. 192° C., is obtained.

Provenance & Evidence