Hydrochloric Acid → 4-[[3-Methyl-4-(4-trifluoromethyl-benzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid

HRID 1991152

반응식

HRID 1991152 반응식
C([O:3][C:4](=[O:36])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[C:16]([CH3:32])[CH:15]=2)=[CH:9][C:8]=1[CH2:33][CH2:34][CH3:35])C.[Li+].[OH-].O.Cl>C1COCC1>[CH3:32][C:16]1[CH:15]=[C:14]([S:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:36])=[O:3])=[C:8]([CH2:33][CH2:34][CH3:35])[CH:9]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 591291244-[[3-Methyl-4-(4-trifluoromethylbenzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid ethyl ester

생성물 1

HCID 103000564-[[3-Methyl-4-(4-trifluoromethyl-benzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Compound 4.5 (32.7 g, 63.0 mmol) was dissolved in THF (250 mL). To the solution was added 4N LiOH (31.5 mL, 126 mmol) and the reaction was stirred at room temperature for 1 h, after which time water (31.5 mL) was added, and the reaction mixture was stirred for 30 min. 2N HCl (70 mL) was then added to the reaction and the THF was removed in vacuo. The residue was diluted with hexane (250 mL) with stirring, and the deposited crystals were collected by filtration and recrystallized from EtOAc-hexane to provide 4 (24.12 g). MS APSI m/e: 489 (M−H). 1H NMR (400 MHz) (DMSO-d6) δ 12.90 (1H, brs); 7.76 (2H, d, J=8.2 Hz); 7.67 (2H, d, J=8.2 Hz); 7.20-7.05 (4H, m); 6.99 (1H, d, J=8.6 Hz); 6.81 (1H, d, J=8.4 Hz); 5.23 (2H, s); 4.68 (2H, s); 2.56-2.47 (2H, m); 2.18 (3H, s); 1.60-1.47 (2H, m); 0.85 (3H, t, J=7.4 Hz).

후처리

  1. stirringthe reaction mixture was stirred for 30 min
  2. customthe THF was removed in vacuo
  3. additionThe residue was diluted with hexane (250 mL)
  4. stirringwith stirring
  5. filtrationthe deposited crystals were collected by filtration
  6. customrecrystallized from EtOAc-hexane

출처 및 근거

ORD 기록
ord-ec44bed0c3354017bbb90d98d57a0a75
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645779B2

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