Triphenylphosphine → [4-Aminomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

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Reaction Steps

To a mixture of [4-azidomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (100 mg, 0.29 mmol) was treated with PPh3 on resin (140 mg, about 0.42 mmol) in THF/water (5/1 mL). The reaction mixture was stirred at r.t overnight and filtered off. The filtrate was purified by HPLC, yielded 25 mg of the desired product. 1H NMR (300 MHz, CD3CN) δ 8.44 (s, 1H), 8.30 (d, 1H), 8.12 (s, 1H), 7.50 (s, 1H), 7.36 (s, 1H), 5.71 (m, 1H), 4.24 (s, 2H), 3.04-3.10 (m, 1H), 2.50-2.58 (m, 1H).

Provenance & Evidence