Dimethylcarbamoyl Chloride → Ethyl 2-(4-chloro-6-(dimethylcarbamoyloxy)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

To a solution of ethyl 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (60 mg, 0.22 mmol) in DMF (3 mL) was slowly added NaH (27 mg, 0.66 mmol) at 0° C. The mixture was stirred for 20 min and N,N-dimethylcarbamic chloride (29 mg, 0.27 mmol) was added at 0° C. The reaction mixture was stirred overnight at room temperature and quenched with ice water. The resulting mixture was extracted with EtOAc (2×15 mL) and the combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was used directly in the next step reaction without further purification. MS (ESI) m/z=342 [M+H]+.

1. customat 0° C
2. stirringThe reaction mixture was stirred overnight at room temperature
3. customquenched with ice water
4. extractionThe resulting mixture was extracted with EtOAc (2×15 mL)
5. dry with materialthe combined extracts were dried over anhydrous Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was used directly in the next step reaction without further purification

ORD record

ord-d7cfca97f9ee4868b1209cb9f1052967

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343944B2