Potassium Carbonate → HCID 58292707, compound

HRID 1798114Notes

Reaction equation

HRID 1798114 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.C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]([NH:29][CH3:30])=[O:28]>CN(C=O)C>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][CH2:26][C:27]([NH:29][CH3:30])=[O:28])[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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 667732-chloro-N-methylacetamideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292707HCID 58292707, compoundYield 31.1%

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 (200 mg, 0.8 mmol) in anhydrous DMF (4 mL) was added K2CO3 (165 mg, 1.2 mmol), KI (199.2 mg, 1.2 mmol) and 2-chloro-N-methylacetamide (128.4 mg, 1.2 mmol) at rt. After stirring at room temperature overnight, the resulting mixture was quenched by adding water. The resulting mixture was extract with EtOAc. The extract was washed with brine, dried and concentrated to dryness. The residue was purified by recrystallization from mixture of ethyl acetate and hexane to give 80 mg of pure product as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.11 (s, 1H), 6.87 (s, 1H), 6.86 (br, 1H), 5.61 (d, J=9.2 Hz, 1H), 5.59 (s, 1H), 4.53 (s, 2H), 4.18 (q, 2H), 3.07 (d, 1H), 2.93 (t, 3H), 2.37 (m, 1H), 2.32 (s, 3H). 2.14 (s, 3H) ppm. MS (ESI) m/z=322 [M+H]+.

Workup

  1. customthe resulting mixture was quenched
  2. additionby adding water
  3. extractionThe resulting mixture was extract with EtOAc
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by recrystallization from mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b896753589e74ae2b70bea8eb2114079
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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