Hydrochloric Acid → 4-{[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]methyl}-2,5-difluorobenzoic acid

HRID 1525667노트

반응식

HRID 1525667 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH2:13][C:14]2[C:24]([F:25])=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[C:16]([F:26])[CH:15]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].O1CCCC1.CO.[OH-].[Na+].Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH2:13][C:14]2[C:24]([F:25])=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[C:16]([F:26])[CH:15]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 89619166Ethyl 4-(((5-chloro-6-isopropoxypyridin-3-yl)oxy)methyl)-2,5-difluorobenzoate

생성물 1

HCID 896192574-{[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]methyl}-2,5-difluorobenzoic acid수율 94%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of ethyl 4-{[(5-chloro-6-isopropoxypyridin-3-yl)oxy]methyl}-2,5-difluorobenzoate (Preparation 14, 400 mg, 1.03 mmol) in a mixture tetrahydrofuran/methanol (1/1 10 mL) was added an aqueous solution of sodium hydroxide (2M, 2.6 mL, 5.15 mmol). The reaction was stirred at room temperature for 2 hours and diluted with ethyl acetate (20 mL). An aqueous solution of hydrochloric acid (2M, 10 mL) was added to pH 1. The organic phase was extracted with ethyl acetate (2×10 mL) and the combined organic layers were washed with brine (20 mL), dried over magnesium sulfate, filtered and the solvent removed in vacuo to afford the title compound as a colourless oil (240 mg, 94% over two steps). No further purification undertaken.

후처리

  1. extractionThe organic phase was extracted with ethyl acetate (2×10 mL)
  2. washthe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-785b33d8f3714c919c1b75102caabe2d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085517B2

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