1,2-Dichloroethane → ((2(S)-Benzoylamino-3-methylbutyryl)indan-2-ylamino)acetic Acid t-Butyl Ester

Participants

Reaction Steps

To a solution of compound 722 (500 mg, 0.88 mmol) in CH3CN (6.0 mL) was added diethylamine (455μ, 4.4 mmol) and the reaction allowed to stir for 2 hr. The reaction was concentrated and the residue co-concentrated with toluene (2×) to provide a viscous oil. The residue was dissolved in CH2Cl2 (5 mL) containing DMF (2 mL), treated with benzoic acid (161 mg, 1.32 mmol) followed by EDC (252 mg, 1.32 mmol) and the reaction allowed to stir overnight. The reaction was diluted with EtOAc and washed with H2O. The aqueous layer was re-extracted with EtOAc. The extracts were combined washed with 5% KHSO4, filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with 10% EtOAc:hexane) provided 240 mg of compound 723. ##STR102##

Provenance & Evidence