Dimethylamine → HCID 11384295, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(CBz-Val-amido)-5-fluoro-4-oxo-pentanoic acid (150 mg, 0.39 mmol) in THF (5 ml) was added a solution of 2.0 M dimethylamine in THF (0.2 ml, 0.4 mmol), EDCI (82.2 mg, 0.42 mmol) and HOBT (106 mg, 0.78 mmol) at 0° C. The resulting mixture was stirred for 2 h at 0° C., then was stirred at room temperature overnight. The solution was diluted with ethyl acetate (20 ml), washed with water (4×20 ml), and the organic layer was dried and evaporated. The residue was purified by chromatography over silica gel (hexane-EtOAc, 1:1 to pure EtOAc) to give 10 mg (6%) of the titled compound as a white solid. 1H NMR (DMSO-d6): 8.36-8.30 (m, 1H), 7.45 (d, J=8.1 Hz, 1H), 7.33-7.29 (m, 5H), 5.45-5.09 (m, 2H), 5.03 (bs, 2H), 4.59-4.57 (m, 1H), 3.90-3.82 (m, 1H), 2.94 (bs, 3H), 2.84-2.73 (m, 4H), 1.97-1.93 (m, 1H), 1.25 (bs, 1H), 0.86-0.82 (m, 6H).

Provenance & Evidence