Sodium Chloride → HCID 178501946, compound

Participants

Reaction Steps

Methyl N-[(10R,14S)-14-[6-(3-chloro-2,6-difluorophenyl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl]carbamate: To a solution of 10G (26 mg, 0.038 mmol) in dioxane (2 mL) was added CDI (60.9 mg, 0.376 mmol), TEA (0.262 mL, 1.878 mmol), DMAP (7.4 mg, 0.061 mmol) and sodium chloride (10.97 mg, 0.188 mmol). The reaction mixture was stirred at rt for 15 min. After 15 min, the reaction mixture was heated at 60° C. for 15 h. Aliquot LCMS shows the reaction mixture still contained the starting material and so the reaction mixture was heated at 70° C. for another 8 h. The reaction mixture was then cooled down to rt and diluted with EtOAc. The EtOAc layers were washed with water followed by brine and dried over MgSO4. The organic layers were concentrated and purified by silica gel chromatography. Desired fractions were pooled together and concentrated to yield the desired product (15 mg, 55%) as white solid product. MS (ESI) m/z: 718.1 (M+H)+.

Provenance & Evidence