HCID 53656947, compound → [Isobutyl-(5-methyl-3-methylcarbamoyl-hexanoyl)-amino]-acetic acid benzyl ester

Participants

Reaction Steps

To an ice-cooled solution of 5-methyl-3-methylcarbamoyl-hexanoic acid 2,3,4,5,6-pentafluorophenyl ester (350 mg, 0.99 mmol) in DMF (5 ml) was added isobutylamino-acetic acid benzyl ester (110 mg, 0.49 mmol) with stirring. The reaction mixture was allowed to warm to room temperature and stirred for 2 days then for 3 h at 50° C. The solvent was removed under reduced pressure, the residue was dissolved in ethyl acetate and the solution was washed successively with 1M HCl, 1M Na2CO3 and brine. The organic layer was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel, 50→100% ethyl acetate in hexane) to give the title compound as a colourless oil (130 mg, 70%). 1H-NMR; δ(CDCl3, rotamers), 7.33 (5H, m), 6.17 (1H, m), 5.15 (1H, m), 4.21 (1H, m), 3.91 (1H, m), 3.41-2.95 (2H, br m), 2.81 (2H, m), 2.75 (3H, m), 2.32 (1H, m), 1.91-1.40 (3H, br m), 1.28-1.05 (1H, m) and 0.85 (12H, m).

Provenance & Evidence