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 1754915ノート

反応式

HRID 1754915 の反応式
[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]

参加物

4

反応物 2

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

生成物 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 ester収率 57%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f921afccc4e8420690afd1eca79d34b2
出典データセット
uspto-grants-2015_10
特許番号
US09169254B2

反応ノート

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