m-Tolyl isocyanate → HCID 11812189, compound

Participants

Reaction Conditions

Reaction Steps

0.05 cm3 of 3-methylphenyl isocyanate is added to a solution of 0.08 g of tert-butyl (2S,5R)-1-(2-aminoacetyl)-5-phenylprolinate in 10 cm3 of anhydrous tetrahydrofuran. The reaction mixture is stirred for 3 hours at a temperature in the vicinity of 25° C., the solvent is then evaporated under reduced pressure at 45° C. The crude product obtained is purified by chromatography on silica [eluent: dichloromethane/methanol (98/2 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure. 0.04 g of tert-butyl (2S,5R)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylprolinate is thus obtained, the analytical data for which are in agreement with those for the dextrorotatory enantiomer prepared by chiral stationary phase chromatography of the racemic product, ([α]D20 =±35.6°±0.8° (C=0.11%; MeOH)).

Provenance & Evidence