Triethylamine → HCID 86617874, compound

Participants

Reaction Steps

To a −20° C. solution of tert-butyl (1R)-1-benzyl-3-({2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinoyl}amino)-2-hydroxy-1-methylpropylcarbamate (0.400 g, 0.74 mmol) in 8 mL CH2Cl2/4 mL DMSO was added triethylamine (0.41 mL, 2.96 mmol). After 5 min, a solution of pyridine sulfur trioxide (0.471 g, 2.96 mmol) in 3 mL DMSO was added via cannula. After 16 h at ambient temperature, the reaction was quenched with brine (10 mL) and extracted with Et2O (15 mL). The aqueous layer was back extracted with Et2O (10 mL×2). The combined organics were washed with 10% aqueous sodium bisulfite (10 mL), and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by normal phase chromatography (20->70% EtOAc/hexanes) yielded 0.335 g (84%) of tert-butyl (1R)-1-benzyl-3-({2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinoyl}amino)-1-methyl-2-oxopropylcarbamate as a white solid. NMR (CDCl3, 400 MHz) 7.69 (d, J=1.01 Hz, 1H); 7.51 (d, J=0.92 Hz, 1H); 7.31 (m, 3H); 7.12 (m, 2H); 4.62 (m, 1H); 4.41 (m, 1H); 3.44 (s, 3H); 3.11 (s, 3H); 1.48 (s, 9H); 1.31 (s, 3H); LC/MS [M−C4H7]+=483.

Provenance & Evidence