Acetamide, N-(trimethylsilyl)- → HCID 86587226, compound

Participants

Reaction Steps

To a stirred solution of N-[(3R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-(2-aminoacetyl)amino-β-alanine (600 mg) and N-trimethylsilylacetoamide (770 mg) in acetonitrile (10 mL) was added terephtalic acid monomethyl ester chloride (233 mg) at 4° C. After stirring for 3 hours, the reaction mixture was acidified with 5% aqueous potassium hydrogensulfate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The organic layer was evaporated and the residue was treated with 4 N—HCl in ethyl acetate. The resulting insoluble material was collected by filtration, dried and dissolved in water. The solution was neutralized with an aqueous saturated sodium hydrogencarbonate solution, purified by ODS column chromatography (Daisogel-120sp®) eluting with 5, 10, 15 and 20% CH3CN/H2O and lyophilized to give N-[(3R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-(2-((4-methoxycarbonylbenzoyl)amino)acetyl)amino-β-alanine (500.5 mg, 74.6%) as an amorphous powder.

Provenance & Evidence