Citric Acid → 3-(2-fluoro-4-{[4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzyl]amino}phenyl)propanoic acid

HRID 508054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508054
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:21]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][C:19]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)=[N:18]3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:40][CH2:41][C:42]([O:44]CC)=[O:43].[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:21]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][C:19]([C:30]4[CH:31]=[CH:32][C:33]([C:36]([F:38])([F:37])[F:39])=[CH:34][CH:35]=4)=[N:18]3)=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:40][CH2:41][C:42]([OH:44])=[O:43]

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23157433ethyl 3-(2-fluoro-4-{[4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzyl]amino}phenyl)propanoate

Produkt 1

HCID 231574013-(2-fluoro-4-{[4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzyl]amino}phenyl)propanoic acidAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-(2-fluoro-4-{[4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)benzyl]amino}phenyl)propanoate in ethanol (10 mL) and tetrahydrofuran (10 mL) was added 1 M aqueous sodium hydroxide solution (4 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the mixture was weakly acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane) to give the title compound (620 mg, yield 51%, 2 steps) as a yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d32dbd2cb0074f4e908726e48f024d0d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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