Nitrogen → 2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid

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Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carboxylic acid methyl ester (713 mg, 2.65 mmol) in THF (15 mL) was treated at rt with 1N NaOH (6.7 mL, 6.70 mmol) and the reaction mixture was stirred for 1 h at rt. The solvents were removed under reduced pressure. The residue was treated with sat. aq. NH4Cl, and acidified to pH 4-5 with 1N HCl. The aq. layer was extracted with CH2Cl2 and the combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a white solid. TLC: rf (4:1 CH2Cl2-MeOH)=0.5. LC-MS-conditions 02: tR=0.75 min [M+H]+=256.31.

Provenance & Evidence