2,5-Pyridinedicarboxylic acid, 2-(1,1-dimethylethyl) ester synthesis

Yield:317356-13-1 76%

Reaction Conditions:

with hydrogenchloride;sodium hydroxide in tetrahydrofuran;

Steps:

56 5-[[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]methylamino]pyridine-2-carboxylic Acid

A mixture of methyl 6-tert-butoxycarbonylnicotinate (1.2 g, 5.06 mmol) in THF (15 ml) and 0.25 N NaOH (40 ml, 10 mol) at an ambient temperature for 0.5 hr. The mixture was poured into ice-1N HCl (10 ml). The solid was collected, washed with water and air-died. The crude solid was recrystallized from CHCl₃-EtOH-IPE to afford 6-tert-butoxycarbonylnicotinic acid (850 mg, 76%) as needles. IR (KBr) m/z 3095, 1728, 1705 cm^-1; ¹H-NMR (DMSO-d₆) δ 1.63 (s, 9H), &.09 (m, 1H), 8.17 (m, 1H), 8.42 (dt, J=2.4 and 8.3 Hz, 1H), 9.21 (t, J=2.4 and 8.8 Hz, 1H); MS (FAB) m/z 224 (M⁺+1); Anal. Calcd for C₂₉H₃₃N₃O₆: C, 36.18; H, 3.18; N, 3.84. Found: C, 36.85; H, 3.35; N, 3.79.

References:

US2003/78249,2003,A1