5-Methyl-1,3,4-oxadiazole-2-carboxylic acid potassium salt

Chemical Properties

Off-White Solid

Uses

An intermediate in the preparation of HIV-integrase inhibitors.

Synthesis

Synthesis of potassium 5-methyl-1,3,4-oxadiazole-2-carboxylate (19b): potassium triethylsilanolate (411 mg, 3.20 mmol) was suspended in ethyl ether at room temperature and stirred to form a slurry. Subsequently, ethyl 5-methyl-1,3,4-oxadiazole-2-carboxylate (0.50 g, 3.20 mmol) was added at once. The reaction immediately produced a precipitate, which changed color from white to off-white. The precipitate was separated by filtration, washed with ether and dried to give the title compound as an off-white solid (580 mg, quantitative yield).1H NMR (300 MHz, CDCl3): δ 2.61 (3H, s). 13C NMR (75 MHz, D2O): δ 166.7, 161.3, 159.3, 10.4.

References

[1] Patent: US2009/35324, 2009, A1. Location in patent: Page/Page column 12
[2] Patent: WO2016/127859, 2016, A1. Location in patent: Paragraph 00194
[3] Patent: CN106349233, 2017, A. Location in patent: Paragraph 0243; 0274; 0275; 0276
[4] Patent: WO2006/60711, 2006, A2. Location in patent: Page/Page column 30-31
[5] Patent: WO2006/60731, 2006, A2. Location in patent: Page/Page column 35-36