Dimethyl Sulfoxide → (1-benzylcyclohexyl)methyl(1S)-5-[(4-morpholinylcarbonyl)amino]-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

Participants

Reaction Steps

To a −60° C. solution of 0.034 mL (0.39 mmol) of oxalyl chloride in 1 mL of dichloromethane was added 0.055 mL (0.78 mmol) of dimethylsulfoxide, dropwise. A solution of 110 mg (0.177 mmol) of (1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate in 1 mL of dichloromethane was added dropwise and the reaction stirred for 10 min before 0.12 mL (0.89 mmol) of triethylamine was added dropwise. The reaction was let warm to room temperature and stirred for 15 min before being applied directly to a silica gel column eluting with 3:7 acetone:dichloromethane to afford 90 mg (82%) of (1-benzylcyclohexyl)methyl(1S)-5-[(4-morpholinylcarbonyl)amino]-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate. 1H NMR (300 MHz, 80° C., DMSO-d6) δ 8.91 (m, 1H), 7.15-7.38 (m, 11H), 6.30 (m, 1H) 5.01 (qnt, J=7 Hz, 1H), 4.85 (m, 1H), 3.63-3.72 (m, 2H), 3.54 (t, J=5 Hz, 4H), 3.26 (t, J=5 Hz, 4H), 3.04 (m, 2H), 2.66 (s, 2H), 1.316-1.714 (m, 19H). ES-LCMS m/z 643 (M+Na). HRMS C35H48N4O6 m/z 621.3652 (M+H)Cal; 621.3641 (M+Na)Obs.

Provenance & Evidence