Diisopropylethylamine → HCID 12044226, compound

Participants

Reaction Steps

To a solution of 4-nitro-L-phenylalanine methyl ester hydrochloride (1.527 g, 5.86 mmol), 2-chloro-6-methylbenzoic acid (1.0 g, 5.86 mmol) and DIPEA (3.2 mL, 2.3 g, 18 mmol) in DMF (10 mL) was added HBTU (2.22 g, 5.86 mmol) at room temperature. After 4 hr at room temperature, the reaction mixture was diltuted with ethyl acetate (200 mL) and the organic layer was washed with water (20 mL), 1N HCl, NaHCO3 and brine (2×30 mL for each solvent) and dried over NaSO4. After removal of the solvent, the residue was purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:2), to give N-(2-chloro-6-methylbenzoyl)-4-nitro-L-phenyl alanine methyl ester (1.71 g, 4.50 mmol, 77.6%). mp, 123-4° C. Analysis (C18H17ClN2O5) calcd.: C, 57.38, H, 4.55, N, 7.43. Found: C, 57.11, H, 4.58, N, 7.27.

Provenance & Evidence