Hydrochloric Acid → (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-one

HRID 403253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403253
C(=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:32])=[C:19]([C@:21]2([CH3:31])[C:27]([F:29])([F:28])[CH2:26][O:25][CH2:24][C:23](=[O:30])[NH:22]2)[CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:32])=[C:19]([C@:21]2([CH3:31])[C:27]([F:28])([F:29])[CH2:26][O:25][CH2:24][C:23](=[O:30])[NH:22]2)[CH:20]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86670909(R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-6,6-difluoro-5-methyl-[1,4]oxazepan-3-one

Produkt 1

HCID 68226741(R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-6,6-difluoro-5-methyl-[1,4]oxazepan-3-one (intermediate A17D) (308 mg, 0.70 mmol) in dioxane (20 ml) at 23° C. was added 1 M HCl (2.1 ml, 2.1 mmol) was added. After 30 min of stirring, the reaction mixture was poured on sat. NaHCO3-solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to give a dark green oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-one (172 mg, 0.63 mmol, 90%) as a yellow foam. MS (ISP): m/z=275.2 [(M+H)+].

Aufarbeitung

  1. additionwas added
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a dark green oil, which
  8. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-11a21038385a4f328396c2e7654a45b9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748418B2

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