N-({(5S)-3-[4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide → N-({(5S)-3-[4-(1-methyl-2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

HRID 10832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10832
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][CH:9]=2)=[CH:4][C:3]1=[O:25]>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][CH:9]=2)[CH2:4][C:3]1=[O:25]

Komponenten

4

Edukt 1

HCID 69557640N-({(5S)-3-[4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

Produkt 1

HCID 10246970N-({(5S)-3-[4-(1-methyl-2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamideAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of N-({(5S)-3-[4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.170 g. 0.49 mmol) in 20 mL of MeOH is added 0.05 g of 10% palladium on activated charcoal. The mixture is hydrogenated at 50 psi for 16 hours. The reaction mixture is filtered through celite, silica is added and the mixture is concentrated to dryness. The residue is loaded onto a SIM and purified on a Biotage 12S column with 2% MeOH in CH2Cl2 to yield the desired compound (0.165 g, 96%). 1H-NMR (DMSO) δ: 8.25, 7.48, 7.28, 4.70, 4.10, 3.72, 3.40, 3.29, 3.05, 2.84, 2.39, 1.93, 1.83.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered through celite, silica
  2. additionis added
  3. concentrationthe mixture is concentrated to dryness
  4. custompurified on a Biotage 12S column with 2% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-aafc07e1d0ec45f3bf9d814970cd12ea
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094900B2

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