Sodium Azide → (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane

HRID 2407867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407867
CS(O[C@@H:6]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C=O)C>[N:34]([C@H:6]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[N+:35]=[N-:36]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 86678272(S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate

Produkt 1

HCID 86678273(R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate (1 eq) and NaN3 (5 eq) in DMF (0.5 M) was stirred at 100° C. over night. The reaction mixture was filtered and washed with DCM. The filtrate was concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-15% EtOAc/Hex to give (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane as acolorless oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated en vaccuo
  4. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-5f086ede24314a2f9cb2da820c72c744
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08808703B2

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