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Hydrochloric Acid → 3-[4-({4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzyl}oxy)-2-fluorophenyl]propanoic acid

HRID 2110908
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HRID 2110908 반응식
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:14][C:15]2[CH:36]=[CH:35][C:18]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[C:23]([F:34])[CH:22]=3)=[CH:17][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O1CCCC1.Cl>CO>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:14][C:15]2[CH:36]=[CH:35][C:18]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[C:23]([F:34])[CH:22]=3)=[CH:17][CH:16]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23159844ethyl 3-[4-({4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzyl}oxy)-2-fluorophenyl]propanoate

생성물 1

HCID 231599933-[4-({4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzyl}oxy)-2-fluorophenyl]propanoic acid수율 81.7%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

A mixture of ethyl 3-[4-({4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzyl}oxy)-2-fluorophenyl]propanoate (0.73 g, 1.6 mmol), 1 N aqueous sodium hydroxide solution (3.0 mL), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at 60° C. for 1 hr. 1 N Hydrochloric acid (3.0 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained solid was recrystallized from ethyl acetate-hexane to give the title compound (0.61 g, yield 81%) as colorless crystals. melting point 152-153° C., 1H NMR (CDCl3) δ: 1.26 (9H, s), 1.31 (9H, s), 2.55-2.66 (2H, m), 2.83-2.95 (2H, m), 4.96 (2H, s), 5.48 (2H, s), 5.92 (1H, s), 6.56-6.67 (2H, m), 6.84-6.94 (2H, m), 7.00-7.14 (1H, m), 7.26-7.34 (2H, m).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract washed with aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained solid was recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-53ab2c578745469bbe30de25d1143f06
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07517910B2

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