Sodium Hydroxide → 2-(2-Fluoro-4-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester

HRID 1754915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754915
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]([C:30](=[O:32])[NH2:31])([NH:16][C:17](=O)[C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=2[F:28])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CS(C)=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2([N:16]=[C:17]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=3[F:28])[NH:31][C:30]2=[O:32])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 668171244-Carbamoyl-4-(2-fluoro-4-trifluoromethyl-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 668181802-(2-Fluoro-4-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl esterAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A 6 N aqueous NaOH solution (54.8 μL, 323 μmol) was added to a solution of 4-carbamoyl-4-(2-fluoro-4-trifluoromethyl-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 231 μmol) in DMSO (0.3 mL), and the mixture was stirred at room temperature for 27 hours. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution and then diluted with EtOAc, and the organic layer was sequentially washed with H2O and saturated brine. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (CH2Cl2/MeOH=95:5) to give 2-(2-fluoro-4-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester as a white solid (54.5 mg, 57%).

Aufarbeitung

  1. customThe reaction mixture was quenched with a saturated aqueous ammonium chloride solution
  2. additiondiluted with EtOAc
  3. washthe organic layer was sequentially washed with H2O and saturated brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography (CH2Cl2/MeOH=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-f921afccc4e8420690afd1eca79d34b2
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

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