Hydrochloric Acid → HCID 20637706, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL round bottomed flask equipped with a magnetic stirrer was charged with 96 mg of N-((tert-butoxy)carbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanine 77 mg of tert-butyl 3-cyclopentyl-L-phenylalaninate.HCl, and 10 mL of CH2Cl2. The solution was cooled to 0° C. and treated with 48 mg of EDC (Aldrich) followed by 0.026 mL of N-methylmorpholine. The reaction mixture was stirred at 0° C. for 20 min, allowed to warm to RT, and stirred for an additional 2 h. Analysis of the solution by tlc (SiO2, 7:3 hexane:EtOAc) indicated a major new component at Rf=0.54 and four minor components at Rf=0.4, 0.37, 0.16 and 0.0. The solution was concentrated in vacuo to dryness and the residue was subjected to flash chromatography on 50 g of silica gel to afford 73 mg (46%) of tert-butyl N-((tert-butoxy)carbonyl)-4-(bis(2-chloroethyl)amino)-L-phenylalanyl-(3-cyclopenty)-L-phenylalaninate as a thick semi-solid.

Provenance & Evidence