Azidomethyl 2,2-dimethylpropanoate → (4-((6-(1H-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl pivalate

HRID 80641

Reaktionsgleichung

Reaktionsgleichung von HRID 80641
[C:1]([O:7][CH2:8][N:9]=[N+:10]=[N-:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].O.C(O)CCC.[CH2:18]([O:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[CH:32]=[N:31][N:30]=[N:29]2)=[N:26][CH:27]=1)[C:19]#[CH:20].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([O:7][CH2:8][N:9]1[CH:20]=[C:19]([CH2:18][O:21][C:22]2[CH:27]=[N:26][C:25]([N:28]3[CH:32]=[N:31][N:30]=[N:29]3)=[CH:24][CH:23]=2)[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 11521126Azidomethyl 2,2-dimethylpropanoateHCID 22253497Water butanolHCID 23667548Sodium AscorbateHCID 577084315-(Prop-2-ynyloxy)-2-(1H-tetrazol-1-yl)pyridine

Produkt 1

HCID 57708433(4-((6-(1H-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl pivalate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittel3×

Versuchsvorschrift

To a solution of azidomethyl pivalate (4.26 g, 27.1 mmol) in 1:1 text -butanol water (90 mL total) was added 5-(prop-2-ynyloxy)-2-(1H-tetrazol-1-yl)pyridine (5.45 g, 27.1 mmol), sodium ascorbate (1.4 mL of a 1M solution in water) and copper sulfate (1.4 mL of a 1M solution in water). The solution was stirred at room temperature for 72 hours. Water was added and the suspension was extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford the expected product which was used in the next step without further purification. 1H NMR (DMSO-d6): δ 10.07 (1H, s), 8.43-8.41 (2H, m), 8.00 (1H, d, J=8.8 Hz), 7.88 (1H, dd, J=3.2, 8.8 Hz), 6.32 (2H, s), 5.38 (2H, s), 1.08 (9H, s).

Aufarbeitung

  1. extractionthe suspension was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6cb9a023f229469fa1e8821c6da6f32f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846675B2

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