Acetic Anhydride → Ethyl 2-(6-(5-acetamido-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

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Reaction Steps

To a solution of ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (70 mg, 0.2 mmol) in DCM (10 mL) was added Et3N (0.11 ml) and acetic anhydride (0.08 mL). The mixture was stirred at room overnight. The mixture was concentrated and precipitate was filtered and washed with a mixture of hexane and ethyl acetate to afford the product as a light yellow solid (59 mg). 1H NMR (DMSO-d6) δ 12.44 (s, 1H), 9.28 (s, 1H), 7.4 (s, 1H), 7.26 (s, 1H), 5.54 (d, 1H), 4.03 (q, H) 3.14 (dd, 1H), 2.48 (d, 1H), 2.35 (s, 3H), 2.13 (s, 3H), 1.11 (t, 3H); MS found: (M+H)+=392.1.

Provenance & Evidence