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Method D: Twenty one mM acid chloride were dissolved in 10 ml tetrahydrofuran and added to a mixture of 20 mM 2-amino-5-chloropyridine, 3.5 ml (25 mM) triethylamine and 40 ml tetrahydrofuran as described in method C. The mixture was stirred for 15 min prior to filtration to remove the triethylamine hydrochloride. The solid was washed with 10 ml tetrahydrofuran and the combined filtrates evaporated under reduced pressure. In case of the oxalyl derivate, the residue was dissolved in 90 ml hot 95% ethanol and the solution filtered while still hot. The mixture was stirred and 40 mM KOH dissolved in 10 ml water were added at a rate that the temperature did not rise above 40C. The reaction was completed by stirring for a further 10 min. The product separated as white potassium salt which was collected by suction. The precipitate was dissolved in 100 ml (iodo derivative: 250 ml) hot water and filtrated. Hydrochloric acid was added to the hot filtrate until pH2. The product separated as free acid during incubation at 4C overnight. The product was further purified by recrystallisation from 95% ethanol. In case of the malonyl and adipoyl derivatives, the residue was dissolved in 200 ml MeOH and filtrated. The solution was placed in a triple-necked round bottom flask equipped with a reflux condenser, a dropping funnel and a thermometer and heated to 50C. While stirring the mixture, 40 mM KOH dissolved in 40 ml water were rapidly added through the dropping funnel and the temperature maintained at 50C. The reaction was completed by stirring at the same temperature for an additional 10 min. The surplus of KOH was neutralised by addition of 40 mM NH4Cl dissolved in 10 ml water. Most solvent was removed under reduced pressure and the residue dissolved in water (about 200 ml) and filtered. Formic acid was added to the clear filtrate until pH3. The product separated as white crystals during incubation at 4C overnight. The malonyl and adipoyl derivatives were purified by recrystallisation from 95% or 50% ethanol, respectively.
With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20℃; for 3h;
To a solution of methyl 2-((5-chloropyridin-2-yl)amino)-2-oxoacetate (Int 10/3) (0.50 g, 2.30 mmol) in THF (8 mL), MeOH (5 mL) and H20 (5 mL) was added LiOH H20 (289 mg, 6.90 mmol). The mixture was stirred at rt for 3 h. It was concentrated and the residue was diluted with H2O (10 mL). It was acidified with 1 N HCI solution to pH = 6-7 and extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated to give the title compound as a yellow solid.
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