Sodium Hydroxide → 2-[5-(2-Ethyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid

HRID 889688ノート

反応式

HRID 889688 の反応式
C([O:3][C:4](=[O:34])[CH:5]([C:10]1[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:13]=[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH3:23])[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+]>CO>[CH2:22]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][N:16]1[C:14]1[CH:15]=[C:10]([CH:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:4]([OH:34])=[O:3])[CH:11]=[C:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)[CH:13]=1)[CH3:23]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 57665995HCID 57665995、化合物

生成物 1

HCID 252679802-[5-(2-Ethyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-[5-(2-ethyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid ethyl ester (12 mg, 0.03 mmol) in MeOH (1 mL) was added 3N NaOH (0.200 mL) and heated to 60° C. for 2 h. The reaction was concentrated in vacuo to remove MeOH. The thick liquid was acidified to pH=2 by 2N HCl. The resulting acidic solution was extracted with EtOAc. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by Gilson reverse phase column chromatography to obtain 2-[5-(2-ethyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid. 1H-NMR (CDCl3): δ 0.80 (t, 3H), 0.92 (d, 6H), 1.44 (m, 1H), 1.50 (q, 1H), 1.58-1.69 (m, 3H), 1.89 (m, 1H), 2.02 (m, 2H), 2.14-2.26 (m, 2H), 3.29 (m, 2H), 3.68-3.81 (m, 2H), 7.59-7.73 (m, 7H); Calcd for C26H32F3NO2 (M+H) 448.53, Found 448.34

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. customto remove MeOH
  3. extractionThe resulting acidic solution was extracted with EtOAc
  4. dry with materialThe organic fraction was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by Gilson reverse phase column chromatography

出典と根拠

ORDレコード
ord-cca413837bd8468697e5f7ace4b06c6d
出典データセット
uspto-grants-2012_08
特許番号
US08252935B2

反応ノート

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