Triphenylphosphine → Ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)thio]butyl)benzyl)oxy]phenyl)propanoate

HRID 732202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732202
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16](O)[CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[SH:28][C:29]1[S:30][CH:31]=[C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([S:28][C:29]3[S:30][CH:31]=[C:32]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:33]=3)[CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23143246Ethyl 3-(2-fluoro-4-{[4-(1-hydroxybutyl)benzyl]oxy}phenyl)propanoateHCID 1785278304-phenyl-1,3-thiazole-2-thiol

Produkt 1

HCID 23143245Ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)thio]butyl)benzyl)oxy]phenyl)propanoateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-(2-fluoro-4-{[4-(1-hydroxybutyl)benzyl]oxy}phenyl)propanoate (0.500 g, 1.34 mmol), 2-mercapto-4-phenylthiazole (0.284 g, 1.47 mmol) and triphenylphosphine (0.700 g, 2.67 mmol) in toluene (10 mL) was added diethyl azodicarboxylate (40% toluene solution, 1.21 mL, 2.67 mmol) with stirring at room temperature, and the mixture was stirred at the same temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (0.555 g, yield 76%) as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 1.5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

Quellen und Nachweise

ORD-Eintrag
ord-f3e6d1265df94055bd9fef472cf12f23
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585880B2

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