Sodium Hydroxide → {5-Fluoro-2-[(3-Nitrobenzyl)carbamoyl]phenoxy}acetic Acid

HRID 2229542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229542
C([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14](=[O:26])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)C.[OH-].[Na+]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:8]([C:14](=[O:26])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[C:7]([CH:12]=1)[O:6][CH2:5][C:4]([OH:27])=[O:3]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22093485[5-Fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester

Produkt 1

HCID 9798381{5-Fluoro-2-[(3-Nitrobenzyl)carbamoyl]phenoxy}acetic AcidAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of [5-fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (3.3 g, 8.77 mmol) in ethanol (40 mL) was treated with aq 2 N NaOH (24 mL, 47.8 mmol). After stirring for 4 h, the solution was concentrated in vacuo until most of the ethanol was removed, and the mixture was acidified to pH of 1 with 2 N HCl. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO; and concentrated to give [5-fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid as an off-white solid (3.00 g, 98%): mp 148-151° C.; Rf 0.39 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 9.20 (t, J=6.3 Hz, 1H) 8.18 (s, 1H), 8.09 (dd, J1=7.2 Hz, J2=2.7 Hz, 1 H), 7.90 (dd, J1=8.7 Hz, J2=7.0 Hz, 1H), 7.79 (d, J=7.5 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.08 (dd, J1=10.8 Hz, J2=2.1 Hz, 1H), 6.91 (dt, J1=8.7 Hz, J2=2.4 Hz, 1H), 4.89 (s, 2H), 4.62 (d, J=6 Hz, 2H). ESI-LC/MS m/z calcd for C16H13FN2O6: 348.3; Found 347.0 (M−1)−. Anal. calcd for C16H13FN2O6: C, 55.18; H, 3.76; N, 8.04. Found C, 55.02; H, 3.79; N, 7.98.

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo until most of the ethanol
  2. customwas removed
  3. extractionAfter extracting with ethyl acetate
  4. washthe organic layer was washed with saturated aq NaCl
  5. dry with materialdried over MgSO
  6. concentrationand concentrated

Quellen und Nachweise

ORD-Eintrag
ord-8d53dfec0e844d499090e5b13b693437
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420426B1

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