Diisopropylethylamine → HCID 58981745, compound

Participants

Reaction Steps

73 mg (0.18 mmol) of N-[(2S,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride & N-[(2R,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride was slurried in 3.5 mL of anhydrous dimethylformamide. Addition of 80 mg (0.18 mmol) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl 4-nitrophenyl carbonate followed by 0.14 mL (0.72 mmol) of diisopropylethylamine resulted in a light yellow solution, which was stirred for 3 d. It was then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, and the solution was washed with a saturated aqueous sodium bicarbonate solution., dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with a methanol:chloroform solution (1:9) to afford 54 mg (50%) of (1 S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate. ES-LCMS n/z 622 (M+Na) retention time=3.96 min.

Provenance & Evidence