Hydrochloric Acid → (4-Aminomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid

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Reaction Steps

To a solution of (4-azidomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (15 mg) in THF/water (2:1, 1 mL) was added 10% Pd/C (5 mg), and a drop of 1N HCl. The reaction was degassed and stirred under hydrogen overnight and filtered off. The filtrate was purified by HPLC, yielded 2 mg of product. MS (ESI) m/z: 237.9 [M+1]+; 1H NMR (300 MHz, CD3OD) δ 8.25 (s, 3H), 7.06 (d, 1H), 6.98 (d, 1H), 8.20 (s, 1H), 5.68 (dd, 1H), 4.17 (s, 2H), 3.67 (s, 1H), 2.99-3.04 (m, 1H), 2.71-2.87 (m, 2H), 2.45-2.52 (m, 1H).

Provenance & Evidence