Sodium Hydroxide → 4-((3-cyclohexyl-5-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-1-yl)methyl)benzoic acid

HRID 1669826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669826
[CH:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:9]([CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.O>[CH:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:21])([F:22])[F:20])=[CH:16][CH:17]=3)[N:9]([CH2:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 67335595methyl 4-({3-cyclohexyl-5-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-yl}methyl)benzoate

Produkt 1

HCID 533232474-((3-cyclohexyl-5-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-1-yl)methyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 0.19 g methyl 4-({3-cyclohexyl-5-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-yl}methyl)benzoate from Step C Example 1 in 6 mL ethanol and 2.5 mL water was treated with 2.4 equivalents of 5 N NaOH solution till the hydrolysis was complete based on HPLC. After evaporating ethanol under reduced pressure, the residue was acidified with 20% molar excess of 2 N HCl to precipitate the acid product. Extract the reaction mixture with 2×35 mL EtOAc. Wash the combined organic layer with saturated brine, dry over anhydrous Na2SO4, and evaporate to give the title compound as a white solid. It can be recrystallized from 5:3 MeCN and water to give fine crystalline needles. 1H NMR (CDCl3, 500 MHz) δ 7.89 (d, J=8.3 Hz, 2H), 7.39˜7.42 (m, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.00 (d, J=8.3 Hz, 2H), 6.30 (s, 1H), 5.38 (s, 2H), 2.67 (tt, J=3.5 & 11.5 Hz, 1H), 1.97˜2.01 (m, 2H), 1.80˜1.85 (m, 2H), 1.71˜1.75 (m, 1H), 1.38˜1.53 (m, 4H), 1.26˜1.33 (m, 1H). LC-MS: 2.47 min. (M+H=445.3).

Aufarbeitung

  1. customAfter evaporating ethanol under reduced pressure
  2. customto precipitate the acid product
  3. extractionExtract the reaction mixture with 2×35 mL EtOAc
  4. washWash the combined organic layer with saturated brine
  5. dry with materialdry over anhydrous Na2SO4
  6. customevaporate

Quellen und Nachweise

ORD-Eintrag
ord-ed8adb40a754470d8c626758ac059d49
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989475B2

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