Hydrochloric Acid → 2-(4-Chloro-6-(ethoxycarbonyloxy)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

To the suspension of the crude 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid (180 mg, 0.74 mmol) and NaOH (30 mg, 0.74 mmol) in 8 mL H2O was added ethyl chloroformate (96 mg, 0.89 mol) dropwise at 0° C. The reaction mixture was stirred at room temperature for 30 min and acidified to pH=5.0 using 1N HCl. The resulting mixture was extracted with EtOAc (3×10 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as an off-white powder (50 mg, yield: 21.5%, two steps). 1H NMR (400 MHz, DMSO) δ12.43 (s, 1H), 9.50 (s, 1H), 7.55 (d, J=2.4 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H), 5.52 (m, 1H), 4.28 (m, 2H), 3.19 (m, 1H), 2.36 (m, 1H), 1.31 (t, J=7.0 Hz, 1H).

1. extractionThe resulting mixture was extracted with EtOAc (3×10 mL)
2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
3. concentrationconcentrated in vacuo
4. customThe residue was purified by prep HPLC

ORD record

ord-3b8797c3345a4b82b7c979b4ce82db85

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343944B2