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

HRID 1928592Notes

Reaction equation

HRID 1928592 reaction equation
[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)(C)(C)C.[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]

Participants

7

Reactant 4

HCID 11521126Azidomethyl 2,2-dimethylpropanoateHCID 23667548Sodium AscorbateHCID 577084315-(Prop-2-ynyloxy)-2-(1H-tetrazol-1-yl)pyridineHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

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

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent3×

Procedure

To a solution of azidomethyl pivalate (4.26 g, 27.1 mmol) in 1:1 tert-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).

Workup

  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

Sources & evidence

ORD record
ord-ab95be482abf409eac2209d7effad6cd
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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