Ethyl 2-(6-(5-cyano-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate → [6-(5-Aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

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Reaction Steps

To a solution of [6-(5-cyano-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.41 g, 1.14 mmol) in ethanol (10 mL) was added 10% Pd/C (0.036 g, 0.34 mmol) and the suspension was hydrogenated at 50 psi for 3 hours. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to give [6-(5-aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.22 g, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.43 (s, 1H), 8.69 (br. s., 3H), 7.51 (d, J=2.26 Hz, 1H), 7.34 (d, J=1.94 Hz, 1H), 5.58 (dd, J=8.92, 2.55 Hz, 1H), 4.41 (s, 2H), 4.05 (q, J=7.14 Hz, 2H), 3.16 (dd, J=16.72, 1.75 Hz, 1H), 2.35-2.42 (m, 1H), 2.35 (s, 3H), 1.14 (t, J=7.15 Hz, 3H).

Provenance & Evidence