Lithium Hexamethyldisilazide → (5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-(hydroxymethyl)-oxazolidin-2-one

HRID 1452598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452598
C(OC(=O)NC1C=CC(N2C=[C:20]([S:22][CH3:23])[N:19]=N2)=C(F)C=1)C1C=CC=CC=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:36][C:37]1[CH:38]=[C:39]([N:49]2[CH2:53][C@H:52]([CH2:54][OH:55])[O:51][C:50]2=[O:56])[CH:40]=[CH:41][C:42]=1[N:43]1[CH:47]=NC(C)=[N:44]1>>[F:36][C:37]1[CH:38]=[C:39]([N:49]2[CH2:53][C@H:52]([CH2:54][OH:55])[O:51][C:50]2=[O:56])[CH:40]=[CH:41][C:42]=1[N:43]1[CH:47]=[C:20]([S:22][CH3:23])[N:19]=[N:44]1

Komponenten

4

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 57526960[3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl] carbamic acid benzyl ester2×HCID 57526987(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one

Produkt 1

HCID 57526965(5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-(hydroxymethyl)-oxazolidin-2-one

Versuchsvorschrift

[3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl] carbamic acid benzyl ester (Intermediate 49) (27.4 g, 76.5 mmol), LiHMDS (1M in THF, 91 ml) and R-(−)-glycidyl butyrate (11.5 g, 79.7 mmol) were reacted following the procedure for Intermediate 25 to give the crude title compound (19.4 g), which was used without further purification.

Quellen und Nachweise

ORD-Eintrag
ord-8b4d0cc5daef42b2b77b9f71a236adf0
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473699B2

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