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 1754915노트

반응식

HRID 1754915 반응식
[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]

참가 물질

4

반응물 2

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

생성물 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 ester수율 57%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f921afccc4e8420690afd1eca79d34b2
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

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