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

HRID 131062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131062
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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]−.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0c58c14649864b10b96976ff1d6cfd77
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384558B2

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