Trifluoroacetic acid → 2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)oxy]acetic acid

HRID 131062Notes

Reaction equation

HRID 131062 reaction equation
[C:1]1(=[O:20])[N:5]([O:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12.FC(F)(F)C(O)=O>ClCCl>[C:4]1(=[O:15])[N:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])[C:1](=[O:20])[C:2]2=[CH:19][CH:18]=[CH:17][CH:16]=[C:3]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate2×

Product 1

HCID 107989942-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)oxy]acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl phthalimidooxyacetate (compound 8) (0.5 g, 1.8 mmol) was dissolved in dichloromethane (5 mL), and trifluoroacetic acid (1.5 mL) was added, as illustrated in FIG. 6. The mixture was stirred at RT for one hour and evaporated to dryness. The residue was azeotroped with chloroform (3 times) to yield a white solid weighing 0.393 g (100% yield). The compound was characterized by NMR and MS as follows: 1) C-NMR (d-DMSO): 73.73, 124.13, 129.43, 135.65, 163.46, 168.87 ppm; and 2) H-NMR (d-DMSO): 4.76 (s, 2H); 7.86 (s, 4H) ppm; and 3) MS (ESI): 220.0 [M−H]−, 463.1 [2M-2H+Na]−.

Workup

  1. customevaporated to dryness
  2. customThe residue was azeotroped with chloroform (3 times)
  3. customto yield a white solid

Sources & evidence

ORD record
ord-0c58c14649864b10b96976ff1d6cfd77
Source dataset
uspto-grants-2008_06
Patent number
US07384558B2

Reaction notes

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