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

HRID 457954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457954
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 MgSO4 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, 1 H) 8.18 (s, 1 H), 8.09 (dd, J1=7.2 Hz, J2=2.7 Hz, 1 H), 7.90 (dd, J1=8.7 Hz, J2=7.0 Hz, 1 H), 7.79 (d, J=7.5 Hz, 1 H), 7.61 (t, J=7.8 Hz, 1 H), 7.08 (dd, J1=10.8 Hz, J2=2.1 Hz, 1 H), 6.91 (dt, J1=8.7 Hz, J2=2.4 Hz, 1 H), 4.89 (s, 2 H), 4.62 (d, J=6 Hz, 2 H). 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 MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-57ca775d10d84d779b76a384bee12439
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189749B2

Notizen zur Reaktion

Wird geladen…