Pyridine → HCID 53473320, Verbindung

HRID 2037539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037539
[NH2:1][CH2:2][CH2:3][C@@:4]1([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.N1C=CC=CC=1.[C:40](OC(=O)C)(=[O:42])[CH3:41]>C(Cl)Cl>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:3][CH2:2][NH:1][C:40](=[O:42])[CH3:41])([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 53473235HCID 53473235, Verbindung

Produkt 1

HCID 53473320HCID 53473320, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of (R)-6-(2-aminoethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (120 mg, 0.264 mmol) and pyridine (41 mg, 0.528 mmol) in anhydrous CH2Cl2 (5 mL) was dropwise added acetic anhydride (30 mg, 0.291 mmol) in anhydrous CH2Cl2 (5 mL) at 0° C. under nitrogen. The above mixture was allowed to stir for overnight at ambient temperature. The mixture was diluted with CH2Cl2 and washed with water. The organic layer was dried over Na2SO4 and concentrate to give the crude product, which was purified by preparative TLC to give N-(2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl)acetamide (60 mg, 46%).

Aufarbeitung

  1. customat 0° C.
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrate
  5. customto give the crude product, which
  6. customwas purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-2efa0b374e794a3ba54876a01e79e098
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575156B2

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