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

HRID 889755노트

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HRID 889755 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-45d46067b91f4f39965c205d13222aa1
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252935B2

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