Sodium Azide → (S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

HRID 2091519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091519
CS(O[CH2:6][CH2:7][C@@:8]1([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:16])[CH2:10][CH2:9]1)(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[N:28]([CH2:6][CH2:7][C@@:8]1([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:16])[CH2:10][CH2:9]1)=[N+:29]=[N-:30]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 866587272-((S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate

Produkt 1

HCID 58485263(S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-oneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-((S)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate (273 mg, 0.68 mmol) in DMF (5 mL) was added NaN3 (133 mg, 2.04 mmol), and the mixture was refluxed overnight. The reaction was quenched with H2O, and the pH of the mixture was adjusted to >9 with 1N aq NaOH. The mixture was extracted with EtOAc (3×). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated to give (S)-6-(2-azidoethyl)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (219 mg, 93%). 1H NMR (CDCl3): 0.61-0.69 (s, 9H), 1.02-1.08 (d, 3H), 1.98-2.14 (m, 3H), 2.23-2.32 (m, 1H), 2.51-2.61 (m, 1H), 2.91-3.02 (m, 1H), 3.06-3.13 (m, 1H), 3.41-3.52 (m, 1H), 4.33-4.42 (m, 1H), 6.98-7.03 (m, 2H), 7.21-7.24 (m, 2H).

Aufarbeitung

  1. temperaturethe mixture was refluxed overnight
  2. customThe reaction was quenched with H2O
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fccc06722d494fb5ae7ddaa3e9040c75
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440658B2

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