Sodium Hydroxide → 2-{2-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-isoindol-1-yl}acetic acid

HRID 1592768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592768
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH2:17][C:18]([O:20]C)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH2:17][C:18]([OH:20])=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58777840tert-Butyl 1-(2-methoxy-2-oxoethyl)isoindoline-2-carboxylate

Produkt 1

HCID 587778602-{2-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-isoindol-1-yl}acetic acidAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 1-methoxycarbonylmethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (52.6 g, 180.5 mmol) in MeOH (500 mL) was added 1 N NaOH (199 mL, 199.0 mmol). The mixture is stirred at r.t. for about 48 hours and then concentrated to dryness. The resulting residue was dissolved in water (300 mL) and extracted with diethyl ether (2×). The aqueous portion was acidified to pH 2 with 10% aqueous sodium bisulfate and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated to dryness to afford about 49.8 g of the final compound (99%). EIS-MS 276 [M−1].

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting residue was dissolved in water (300 mL)
  3. extractionextracted with diethyl ether (2×)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fb5da9fc9307488ca921fd3c3d90f3bc
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291619B2

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