Hydrochloric Acid → Ethyl 3-chloro-6-(pivalamidomethyl)picolinate

Participants

Reaction Steps

A solution of ethyl 6-(((tert-butoxycarbonyl)amino)methyl)-3-chloropicolinate (100 mg, 0.318 mmol) in EtOAc saturated with HCl (1 mL) was stirred at rt for 1 h. The reaction mixture was concentrated and the concentrate was dissolved in CH2Cl2 (2 mL). The solution was treated with DIPEA (0.5 mL) followed by pivaloyl chloride (38 mg, 0.318 mmol) at 0° C. The reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc and was washed with H2O and brine. The organic layer was separated, dried, filtered and concentrated to afford 85 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.26 (br t, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.1 Hz, 1H), 4.40-4.31 (m, 4H), 1.33-1.10 (m, 12H).

Provenance & Evidence