Hydrochloric Acid → tert-Butyl 3-(3-(2H-tetrazol-5-yl)phenethoxy)propanoate

Participants

Reaction Conditions

Reaction Steps

Triethylamine hydrochloride (2.09 g) was added in one portion to a mixture of tert-butyl 3-(3-cyanophenethoxy)propanoate [Example 7, Step i)] (1.74 g), sodium azide (0.99 g) and tert-butanol (12.64 mL), and sealed into a microwave tube. The reaction was heated to 140° C., over a period of 2 h in the microwave reactor. The reaction mixture was diluted with water and acidified with 2M hydrochloric acid (5 mL). The mixture was extracted with DCM and the organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 20-100% ethyl acetate in isohexane, then elution gradient 0-10% methanol in DCM to afford the subtitled compound (1.77 g). 1H NMR (300 MHz, CDCl3) δ 8.11 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 7.44 (t, J=7.7 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 3.79 (t, J=5.3 Hz, 2H), 3.75 (t, J=5.6 Hz, 2H), 2.96 (t, J=5.2 Hz, 2H), 2.63 (t, J=5.3 Hz, 2H), 1.48 (s, 9H).

Provenance & Evidence