Diisopropylcarbodiimide → 3-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)pyrrolidine

Participants

Reaction Steps

A solution of 1-(4-chlorobenzyl)-3-{(glycylamino)methyl}pyrrolidine (0.050 mmol) in CHCl3 (1.35 mL) and tert-butanol (0.05 mL) was treated with 2-amino-4,5-difluorobenzoic acid (0.060 mmol), diisopropylcarbodiimide (0.060 mmol), and HOBt (0.060 mmol). The reaction mixture was stirred at room temperature for 19 h. The mixture was loaded onto Varian™ SCX column, and washed with CH3OH/CHCl3 1:1 (10 mL) and CH3OH (10 mL). Product was eluted off using 2 N NH3 in CH3OH (5 mL) and concentrated to afford 3-[{N-(2-amino-4,5-difluorobenzoyl)glycyl}aminomethyl]-1-(4-chlorobenzyl)pyrrolidine (Compound No. 1506) (22.0 mg, quant): The purity was determined by RPLC/MS (92%); ESI/MS m/e 437 (C21H23ClF2N4O2).

Provenance & Evidence