1(3H)-Isobenzofuranone, 3-bromo- → HCID 69584846, compound

HRID 2212440Notes

Reaction equation

HRID 2212440 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>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]([OH:12])=[C:8]([O:13][CH:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:28](=[O:29])[O:27]2)[CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 69584846HCID 69584846, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of compound 108 (380 mg, 1.1 mmol), bromophthalide (213 mg, 1 mmol) and CsHCO3 (325 mg, 1 mmol) in acetone was stirred at room temperature 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. After removing the solvent under reduced pressure, the resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min. After removing the solvent, the resulting residue was purified by reverse phase preparative HPLC to afford two separated stereoisomers 113 (123 mg) and 114 (120 mg), respectively. Compound 113: 1H NMR (CD3OD, 400 MHz): 1.43 (s, 3H), 2.98 (dd, 2H), 3.80 (s, 3H), 6.62–7.20 (m, 4H), 7.66–7.95 (m, 4H). MS (ESI) m/z 373.25 (M+H+) and Compound 114:1H NMR (CD3OD, 400 MHz): 1.44 (s, 3H), 2.99 (dd, 2H), 3.84 (s, 3H), 6.80–7.18 (m, 4H), 7.69–7.93 (m, 4H). MS (ESI) m/z 373.25 (M+H+).

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. customAfter removing the solvent under reduced pressure
  6. additionthe resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min
  7. customAfter removing the solvent
  8. customthe resulting residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-0a27c8d6ea70404193d099ee63c5e866
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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