Potassium Carbonate → (3-{4-[(2-Chloro-3-(trifluoromethyl)benzyl)-(2,2-diphenylethyl)-amino]butyl}phenyl)-acetic Acid

HRID 902624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902624
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=1.[C:27]1([CH:33]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:34][NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[C:38]=2[Cl:47])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Cl:47][C:38]1[C:39]([C:43]([F:44])([F:45])[F:46])=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][N:35]([CH2:34][CH:33]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:26])[CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 58913799(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amineHCID 86598282(3-[4-(Toluene-4-sulfonyloxy)butyl]phenyl}acetic acid methyl ester

Produkt 1

HCID 59701454(3-{4-[(2-Chloro-3-(trifluoromethyl)benzyl)-(2,2-diphenylethyl)-amino]butyl}phenyl)-acetic AcidAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of {3-[4-(toluene-4-sulfonyloxy)butyl]phenyl}acetic acid methyl ester, (2,2-diphenylethyl)-(2-chloro-3-trifluoromethylbenzyl)amine (73 mg, 0.19 mmol), and potassium carbonate (26 mg, 0.21 mmol) in acetonitrile (5 ml) was stirred and heated to 50° C. for 5 hr. The reaction was cooled, diluted with water, and extracted with diethyl ether. The organic extracts were washed with water, dried, and the solvent removed. The residue was chromatographed over silica gel (hexane/methylene chloride/Diethyl ether:60/40/5) to give the title compound as an oil (35 mg, 31%). MS (ESI) 594.2 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with water
  4. customdried
  5. customthe solvent removed
  6. customThe residue was chromatographed over silica gel (hexane/methylene chloride/Diethyl ether:60/40/5)

Quellen und Nachweise

ORD-Eintrag
ord-8c28f4db07e44bd0b627e2cb32184108
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365085B2

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