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

HRID 1798133Notes

Reaction equation

HRID 1798133 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([OH:18])[CH:3]=1.[H-].[Na+].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>CN(C=O)C>[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][C:23](=[O:24])[N:22]([CH3:26])[CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 58292598Ethyl 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292589Ethyl 2-(4-chloro-6-(dimethylcarbamoyloxy)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-d7cfca97f9ee4868b1209cb9f1052967
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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