N-Hydroxyphthalimide → Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

HRID 1374062Notes

Reaction equation

HRID 1374062 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C=O)C>[O:7]=[C:6]1[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[C:3](=[O:12])[N:2]1[O:1][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetateYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-hydroxyphthalimide (10 g, 61.3 mmol), K2CO3 (16.9 g, 122 mmol) and tert-butyl bromoacetate (12 g, 9 mL, 61.3 mmol) in DMF (60 mL) was stirred at room temperature for 3 hours and the solvent was evaporated under high vacuum. The residue was dissolved in EtOAc, washed with brine, dried over Na2SO4 and filtered. The residue after evaporation of the solvent was recrystallized from a mixture of CH2Cl2/EtOAc/hexane to give the title compound (12 g, 71% yield) as a white solid. Mp 140–141° C. 1H NMR (300 MHz, CDCl3) δ 7.80–7.90 (m, 2H), 7.74–7.77 (m, 2H), 4.71 (s, 2H), 1.49 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 166.0, 163.0, 134.7, 128.9, 123.7, 83.0, 73.5, 28.1. Mass spectrum (API-TIS) m/z 278 (MH+), 295 (MNH4+). Anal. calcd. for C14H15NO5: C, 60.64; H, 5.45; N, 5.05. Found: C, 60.47; H, 5.31; N, 4.96.

Workup

  1. customthe solvent was evaporated under high vacuum
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe residue after evaporation of the solvent
  7. customwas recrystallized from a mixture of CH2Cl2/EtOAc/hexane

Sources & evidence

ORD record
ord-02faec326a44489e853b274feb105be0
Source dataset
uspto-grants-2007_01
Patent number
US07163958B2

Reaction notes

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