Sodium Hydroxide → 4-Methyl-2-{4'-trifluoromethyl-5-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-biphenyl-3-yl}-pentanoic acid

HRID 889755ノート

反応式

HRID 889755 の反応式
C([O:3][C:4](=[O:42])[CH:5]([C:10]1[CH:11]=[C:12]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+]>CO>[CH3:8][CH:7]([CH3:9])[CH2:6][CH:5]([C:10]1[CH:11]=[C:12]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][CH:33]=2)[CH:13]=[C:14]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:24][CH:23]=3)[CH2:20][CH2:21]2)[CH:15]=1)[C:4]([OH:42])=[O:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 576659164-Methyl-2-{4'-trifluoromethyl-5-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester

生成物 1

HCID 252669224-Methyl-2-{4'-trifluoromethyl-5-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-biphenyl-3-yl}-pentanoic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of a mixture of 4-methyl-2-{4′-trifluoromethyl-5-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-biphenyl-3-yl}-pentanoic acid ethyl ester and methyl ester (69 mg, 0.12 mmol) in MeOH (2 mL) was added 3N NaOH (0.100 mL) and heated to 50° C. for 14 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 4-methyl-2-{4′-trifluoromethyl-5-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-biphenyl-3-yl}-pentanoic acid. 1H-NMR (DMSO-d6): δ 0.88 (d, 6H), 1.44 (m, 1H), 1.60 (m, 1H), 1.69-1.99 (m, 5H), 2.92 (m, 4H), 3.68 (m, 2H), 4.02 (d, 2H), 7.10 (s, 1H), 7.13 (s, 1H), 7.29 (s, 1H), 7.51 (m, 4H), 7.85 (dd, 4H); Calcd for C31H31F6NO2 (M+H) 564.57, Found 564.3

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-45d46067b91f4f39965c205d13222aa1
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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