Bromoacetic Acid → (2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-acetic acid

HRID 492236Notes

Reaction equation

HRID 492236 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH:18]([OH:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:22][C:23]([OH:25])=[O:24]>C1COCC1>[CH2:3]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]1[O:20][CH2:22][C:23]([OH:25])=[O:24])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 32407432-benzyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 10613926(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-acetic acidYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (1.1 g, 38.5 mmol) in THF (30 mL) at room temperature was added a solution of compound 20 (2.0 g, 8.37 mmol) in THF (15 mL) and the resulting reaction mixture was allowed to stir at room temperature for 1 hour. Thereafter a solution of bromo acetic acid (2.68 g, 19.25 mmol) in THF (5 mL) was added dropwise and the resulting reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture is poured onto water and extracted with ethyl ether (3×100 mL) and the combined ethyl ether extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography (SiO2, 20 to 70% EtOAc-Hexanes eluant) provided 1.0 g of 22 as a clear oil (2.48 g, theoretical, 40% yield).

Workup

  1. customthe resulting reaction mixture
  2. customthe resulting reaction mixture
  3. stirringto stir at room temperature for 18 hours
  4. additionThe reaction mixture is poured onto water
  5. extractionextracted with ethyl ether (3×100 mL)
  6. dry with materialthe combined ethyl ether extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5eea9b605c91468b82e43765d99e2958
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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