Pyridine → HCID 178450889, compound

Participants

Reaction Steps

To a solution of 3-[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)-2-chlorophenyl]propanoic acid (200 mg) in dichloromethane (3.00 mL) was added 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.0700 mL) under ice-cooling, followed by stirring at room temperature for 1 hour. Under ice-cooling, a solution of tert-butyl N-[3-(2-tert-butoxy-2-oxoethyl)phenyl]glycinate (170 mg) and pyridine (0.0500 mL) in dichloromethane (3.00 mL) was added thereto, followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 4-(3-{(2-tert-butoxy-2-oxoethyl)[3-(2-tert-butoxy-2-oxoethyl)phenyl]amino}-3-oxopropyl)-3-chlorophenyl 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoate (210 mg).

Provenance & Evidence