(Diethylamino)sulfur trifluoride → 4,4-Difluoro-4-(4'-methoxy-biphenyl-4-yl)-butyric Acid

HRID 23757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23757
C(O[C:4](=O)[C:5]([F:21])([F:20])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)C.C(N(S(F)(F)F)CC)C.C([O:34][C:35](=[O:52])[C:36](C1C=CC(C2C=CC(OC)=CC=2)=CC=1)=O)C>ClCCl>[F:21][C:5]([F:20])([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)[CH2:4][CH2:36][C:35]([OH:52])=[O:34]

Komponenten

5

Edukt 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 46220012(4'-Methoxybiphenyl-4-yl)difluoroacetic acid ethyl esterHCID 69784836(4'-Methoxy-biphenyl-4-yl)-oxo-acetic acid ethyl ester

Produkt 1

HCID 98395084,4-Difluoro-4-(4'-methoxy-biphenyl-4-yl)-butyric Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Difluoro-(4′-methoxy-biphenyl-4-yl)-acetic acid ethyl ester. Diethylaminosulfur trifluoride (5 mL) is added directly to (4′-methoxy-biphenyl-4-yl)-oxo-acetic acid ethyl ester (3.77 g, 13.3 mmol), prepared as described by Neidlin, et. al., Arzneim.-Forsch. 1983, 33, 691-3. Dichloromethane (2 mL) is added and the mixture is stirred overnight at room temperature. The reaction is diluted with dichloromethane and slowly added to ice water. This mixture is extracted with ethyl acetate twice. The combined organic extracts are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel, 5% EtOAc/hexanes) to give the desired product as a pale yellow solid.

Aufarbeitung

  1. customprepared
  2. extractionThis mixture is extracted with ethyl acetate twice
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (silica gel, 5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e8ca589573444b1b96f7b6fcfff3247d
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852751B2

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