Carbon Dioxide → 3-(Tert-butoxycarbonylamino)-2-methoxyisonicotinic acid

Participants

Reaction Conditions

Reaction Steps

T-butyl (2-methoxypyridin-3-yl)carbamate (8.0 g, 35.7 mmol) and tetramethylethylenediamine (8.3 g, 71.4 mmol) were dissolved in diethyl ether (100 mL). The reaction solution was stirred at −78° C., to which n-butyllithium (2.44 M in hexane, 36.6 mL) was dropwise added at that temperature. The reaction solution was stirred at −78° C. for 1 hour, then gradually heated up to 0° C., and CO2 (solid) was added to it at 0° C. This was stirred at that temperature, and then aqueous saturated ammonium chloride solution was added thereto. The aqueous layer was separated, controlled to have a pH of 1 with 1 N hydrochloric acid added thereto, and extracted with chloroform. All the organic layers were combined, and dried with magnesium sulfate. The solvent was evaporated off under reduced pressure to obtain the intended compound (6.74 g, 70.4%) as a pale yellow oily substance.

Provenance & Evidence