Cesium carbonate → HCID 69585034, compound

HRID 2212441Notes

Reaction equation

HRID 2212441 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([NH:15][NH:16]C(OC(C)(C)C)=O)([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([OH:13])[CH:7]=1.Br[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28](=[O:29])[O:27]1.[C:36]([O-:39])([O-])=[O:37].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:24])[C:4]([NH:15][NH2:16])([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:28](=[O:29])[O:27]2)=[C:8]([O:13][CH:5]2[C:6]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:36](=[O:37])[O:39]2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 69584993HCID 69584993, compound

Product 1

HCID 69585034HCID 69585034, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of compound 108 (170 mg, 0.5 mmol), bromophthalide (213 mg, 1 mmol) and Cs2CO3 (325 mg, 1 mmol) in acetone was stirred at 40° C. for 16 h. After removing the solvent under reduced pressure, the residue was partitioned between 10% citric acid and ethyl acetate. The organic phase was separated and dried over MgSO4, and concentrated to dryness. The resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min. Removal of the solvent and purification of the resulting residue by reverse phase HPLC afford 81 mg of 119 as a mixture of diastereomers. 1H NMR (CD3OD, 400 MHz): 1.50 (3H), 3.10 (2H), 3.84 (3H), 6.86–7.18 (m, 3H), 7.22–7.44 (m, 2H), 7.61–7.95 (m, 8H). MS (ESI) m/z 505.26.

Workup

  1. customAfter removing the solvent under reduced pressure
  2. customthe residue was partitioned between 10% citric acid and ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. additionThe resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min
  7. customRemoval of the solvent and purification of the resulting residue by reverse phase HPLC

Sources & evidence

ORD record
ord-69635607ebb54d5788c38c40073f0c55
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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