Ethyl Acetate → 6-{[2-(1,3-dioxolan-2-ylmethyl)-1-oxa-5-azaspiro[2.3]hex-5-yl]carbonyl}-2,3-difluoro-N-(2-fluoro-4-iodophenyl)aniline

HRID 1717623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717623
CC(C1C=C(C(C)C)C=C(C(C)C)C=1S([O:19][CH:20]([C:27]1(O)[CH2:30][N:29]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[C:34]=2[NH:41][C:42]2[CH:47]=[CH:46][C:45]([I:48])=[CH:44][C:43]=2[F:49])=[O:32])[CH2:28]1)[CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1)(=O)=O)C.[H-].[Na+].C(OCC)(=O)C>O1CCCC1>[O:26]1[CH2:25][CH2:24][O:23][CH:22]1[CH2:21][CH:20]1[C:27]2([CH2:30][N:29]([C:31]([C:33]3[C:34]([NH:41][C:42]4[CH:47]=[CH:46][C:45]([I:48])=[CH:44][C:43]=4[F:49])=[C:35]([F:40])[C:36]([F:39])=[CH:37][CH:38]=3)=[O:32])[CH2:28]2)[O:19]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 866212721-[1-({3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]-2-(1,3-dioxolan-2-yl)ethyl 2,4,6-tris(1-methylethyl)benzenesulfonate

Produkt 1

HCID 866212736-{[2-(1,3-dioxolan-2-ylmethyl)-1-oxa-5-azaspiro[2.3]hex-5-yl]carbonyl}-2,3-difluoro-N-(2-fluoro-4-iodophenyl)anilineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-[1-({3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]-2-(1,3-dioxolan-2-yl)ethyl 2,4,6-tris(1-methylethyl)benzenesulfonate (50 mg, 0.060 mmol) was dissolved in tetrahydrofuran (1 mL) and was cooled to 0° C. Sodium hydride (60 wt % dispersion in oil; 7 mg, 0.18 mmol) was added and the mixture was stirred at 0° C. for 45 minutes. The mixture was quenched with saturated sodium bicarbonate solution and partitioned with ethyl acetate. The aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography (silica gel, 50% ethyl acetate in hexanes) gave 6-{[2-(1,3-dioxolan-2-ylmethyl)-1-oxa-5-azaspiro[2.3]hex-5-yl]carbonyl}-2,3-difluoro-N-(2-fluoro-4-iodophenyl)aniline (31 mg, 0.057 mmol, 94% yield): MS (EI) for C21H18F3IN2O4: 547 (MH+).

Aufarbeitung

  1. customThe mixture was quenched with saturated sodium bicarbonate solution
  2. custompartitioned with ethyl acetate
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. washThe combined organic portion was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-873feddafb544fe6b9e3b815ce5f3763
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803839B2

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