Trifluoroacetic acid → Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxocyclohexyl)methoxy)benzoate

HRID 1849740노트

반응식

HRID 1849740 반응식
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]3[C:25]([CH:26]4[CH2:28][CH2:27]4)=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([F:29])[CH:14]=3)[CH2:7][CH2:6]2)[O:4]CC1.FC(F)(F)C(O)=O>O1CCCC1.O.C(OCC)(=O)C>[CH:26]1([C:25]2[C:13]([O:12][CH2:11][CH:8]3[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]3)=[CH:14][C:15]([F:29])=[C:16]([CH:24]=2)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:28][CH2:27]1

참가 물질

6

반응물 2

HCID 6422Trifluoroacetic acidHCID 86703618Tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate

생성물 1

HCID 86703619Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxocyclohexyl)methoxy)benzoate수율 96%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate (3.16 g, 7.77 mmol) in tetrahydrofuran (10 mL) and water (10 mL) was added trifluoroacetic acid (2.7 mL) and the reaction mixture was stirred for 16 hours at ambient temperature. After diluting the reaction mixture with ethyl acetate (200 mL), the organic phase was washed with 1 N sodium hydroxide solution (2×15 mL), brine (15 mL), and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate under reduced pressure gave a residue which was purified by silica gel column chromatography using 0-40% ethyl acetate in hexanes as eluent to afford the title compound as a colorless oil (2.70 g, 96%): 1H NMR (300 MHz, CDCl3) δ 7.37 (d, J=8.4 Hz, 1H), 6.50 (d, J=12.5 Hz, 1H), 3.90 (d, J=6.0 Hz, 2H), 2.53-2.15 (m, 8H), 2.03-1.92 (m, 1H), 1.73-1.59 (m, 1H), 1.55 (s, 9H), 0.92-0.83 (m, 2H), 0.65-0.58 (m, 2H).

후처리

  1. washthe organic phase was washed with 1 N sodium hydroxide solution (2×15 mL), brine (15 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate under reduced pressure
  4. customgave a residue which
  5. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-44d39c488120480db7dd616f5c74d0d6
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952169B2

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