Methyl iodide → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627167
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][OH:32])[CH:20]=[C:19]1[C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].I[CH3:39]>C(#N)C.[Ag]=O>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[C@H:21]([CH2:31][O:32][CH3:39])[CH:20]=[C:19]1[C:33](=[O:37])[N:34]([CH3:35])[CH3:36])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Komponenten

5

Edukt 2

HCID 6328Methyl iodideHCID 89852042(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

Produkt 1

HCID 89851960(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(methoxymethyl)-5,6-dihydropyridine-1 (2H)-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(dimethylcarbamoyl)-2-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 139, 1.64 g, 3.03 mmol) and silver oxide (2.81 g, 12.13 mmol) were dissolved in acetonitrile (40 mL). To this solution was added iodomethane (1.897 mL, 30.34 mmol) under N2 and stirred over for 5 days protected from the light. The reaction mixture was then filtered through Celite, rinsed with EtOAc, and the crude product was loaded onto silica gel. The product was purified by flash chromatography (0-20% MeOH/DCM) to yield the desired product (1.643 g, 98%) as an off-white solid.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washrinsed with EtOAc
  3. customThe product was purified by flash chromatography (0-20% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-9299cfd2bd314880bb84e91ce18f6a80
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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