Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → (S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 333906

Reaktionsgleichung

Reaktionsgleichung von HRID 333906
[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][C@@:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](CC)(CC)CC)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.[F-].C([N+](CC)(CC)CC)C>C(#N)C>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:34])[CH3:35])([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1)#[CH:20]

Komponenten

4

Edukt 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 66870225HCID 66870225, Verbindung

Produkt 1

HCID 86670541(S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-((triethylsilyl)ethynyl)phenyl)ethyl)-1,3-oxazinan-2-one (184 mg, 0.375 mmol) in acetonitrile (5 mL) was added tetraethylammonium fluoride (112 mg, 2 equiv). The mixture was stirred for 3 h at rt and LC-MS showed the reaction was complete. The mixture was concentrated and purified by chromatography on a 12 g silica cartridge, eluted with a 70-100% EtOAc in hexanes gradient, to afford to afford (S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (128 mg, 91%) as a white solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on a 12 g silica cartridge
  3. washeluted with a 70-100% EtOAc in hexanes gradient
  4. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-bd6968ed48c6466e8db722dd01b4162e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883778B2

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