Dimethylcarbamoyl Chloride → HCID 58292830, compound

HRID 1798134Notes

Reaction equation

HRID 1798134 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.[H-].[Na+].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>CN(C=O)C>[CH3:21][N:22]([CH3:26])[C:23]([O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3][B:2]([OH:1])[C:6]=2[CH:7]=1)=[O:24]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292830HCID 58292830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (500 mg, 2 mmol) in DMF (5 mL) was slowly added NaH (360 mg, 6 mmol) at 0° C. The mixture was stirred for 20 min and N,N-dimethylcarbamic chloride (430 mg, 4 mmol) was added at 0° C. The mixture was stirred overnight at room temperature and quenched with ice water. The resulting mixture was extracted with EtOAc (2×25 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=322 [M+H]+.

Workup

  1. customat 0° C
  2. stirringThe mixture was stirred overnight at room temperature
  3. customquenched with ice water
  4. extractionThe resulting mixture was extracted with EtOAc (2×25 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, MS (ESI) m/z=322 [M+H]+

Sources & evidence

ORD record
ord-ecfdf37678fd45ab87f9b876ecbd6077
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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