Tetrabutylammonium Fluoride → (S)-3-((S)-1-(4-ethynylphenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

HRID 333910

Reaktionsgleichung

Reaktionsgleichung von HRID 333910
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].[OH:19][C:20]([CH3:50])([CH3:49])[CH2:21][C@@:22]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:27][C:26](=[O:28])[N:25]([C@H:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[C:38][Si](C)(C)C)=[CH:33][CH:32]=2)[CH3:30])[CH2:24][CH2:23]1>O1CCCC1>[C:37]([C:34]1[CH:33]=[CH:32][C:31]([C@@H:29]([N:25]2[CH2:24][CH2:23][C@:22]([CH2:21][C:20]([OH:19])([CH3:49])[CH3:50])([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:27][C:26]2=[O:28])[CH3:30])=[CH:36][CH:35]=1)#[CH:38]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 66869815(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

nBu4NF (1 mol/L in tetrahydrofuran, 4.90 mL) was added to a solution of (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one (2.00 g) in tetrahydrofuran (20 mL) at room temperature. The solution was stirred for 1 h at room temperature and then concentrated under reduced pressure. Ethyl acetate was added to the residue and the resulting mixture was washed with water and brine. The organic phase was dried (MgSO4) and the solvent was evaporated to afford the title compound as an oil that solidified on standing. Yield: 1.60 g (95% of theory); LC-MS (Method 1): tR=3.64 min; Mass spectrum (ESI+): m/z=378 [M+H]+.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe resulting mixture was washed with water and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c901cdf00d444534b545e4aa3499ab88
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883778B2

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