Ammonia → (r)-3-((s)-2-(4,4-Dimethyl-3-(4-(3-(2-methylphenyl)ureido)-3-methoxybenzyl)-2,5-dioxoimidazolidin-1-yl)-2-(cyclopropylmethyl)acetylamino)-3-methylpropionamide

Participants

Reaction Steps

131 mg (0.636 mmol) of DCC were added to a solution of 330 mg (0.555 mmol) of the compound of Example 1 and 125 mg (0.926 mmol) of HOBT in 4 mL of absolute DMF, the mixture was stirred at room temperature for 1 hour and then 47 μL (0.555 mmol) of a 25% strength aqueous ammonia solution were added. The mixture was allowed to stand overnight at room temperature, a further 16 μL of a 25% strength aqueous ammonia solution were added and the mixture was stirred for 4 hours. After filtration, the filtrate was concentrated in vacuo, the residue was dissolved in ethyl acetate and the ethyl acetate phase was washed twice in each case with an aqueous KHSO4/K2SO4 solution, a saturated NaHCO3 solution and water. After drying the organic phase over sodium sulfate and filtering, the solvent was removed in vacuo and the residue was chromatographed over silica gel using ethyl acetate. After concentrating the product fractions and freeze drying, 272 mg (82%) of the title compound were obtained.

Provenance & Evidence