Vinyl Acetate → Di-tert-butyl {4-[(3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyridin-3-yl}imidodicarbonate

HRID 924504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924504
[N:1]([C@H:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6][C@H:5]1[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[N+:2]=[N-:3].[CH:40](OC(=O)C)=[CH2:41]>>[C:36]([O:35][C:33]([NH:32][C@H:5]1[C@@H:4]([N:1]2[CH:41]=[CH:40][N:3]=[N:2]2)[C@@H:9]([CH3:10])[CH2:8][N:7]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:6]1)=[O:34])([CH3:38])([CH3:37])[CH3:39]

Komponenten

3

Edukt 2

HCID 7904Vinyl AcetateHCID 86705280tert-butyl (4-((3R,4S,5S)-4-azido-3-((tert-butoxycarbonyl)amino)-5-methylpiperidin-1-yl)pyridin-3-yl)(tert-butoxycarbonyl)carbamate

Produkt 1

HCID 86726945Di-tert-butyl {4-[(3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyridin-3-yl}imidodicarbonateAusbeute 21,1 %

Versuchsvorschrift

A solution of di-tert-butyl (4-{(3R,4S,5S)-4-azido-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}pyridin-3-yl)imidodicarbonate (0.37 g, 0.67 mmol) in acetic acid ethenyl ester (5.50 mL, 59.7 mmol) in a sealed flask was heated at 115° C. for 40 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on silica using a CombiFlash® apparatus (50 to 100% EtOAc in hexanes) to give the sub-title compound (81 mg, 21%). LCMS calc. for C28H44N7O6 (M+H)+: m/z=574.3. Found: 574.4.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on silica using a CombiFlash® apparatus (50 to 100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-97e23d27ffca440ebf7c1e2059acf919
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278950B2

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