Water → HCID 86678197, compound

HRID 1747543Notes

Reaction equation

HRID 1747543 reaction equation
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:6]=[CH:7][C:8]([C:11]#[CH:12])=[N:9][CH:10]=1)[CH3:2].[C:16]([O:22][CH2:23][N:24]=[N+:25]=[N-:26])(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18].O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:16]([O:22][CH2:23][N:24]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:4]([O:3][CH2:1][CH3:2])[O:13][CH2:14][CH3:15])=[CH:10][N:9]=2)[N:26]=[N:25]1)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 962Water2×HCID 11521126Azidomethyl 2,2-dimethylpropanoateHCID 23667548Sodium AscorbateHCID 86678196HCID 86678196, compound

Product 1

HCID 86678197HCID 86678197, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 6386tert-ButanolSolvent

Procedure

In tert-butanol (10 mL) was dissolved 5-(diethoxymethyl)-2-ethynylpyridine (1.41 g, 6.87 mmol) obtained in Step 2. To the solution were added azidomethyl pivalate (1.08 g, 6.87 mmol), water (10 mL), copper (II) sulfate pentahydrate (86.0 mg, 0.343 mmol) and sodium ascorbate (408 mg, 0.343 mmol), and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give (4-(5-(diethoxymethyl)pyridin-2-yl)-1H-1,2,3-triazol-1-yl)methyl pivalate (2.27 g, 91% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-3335665719ae4230a043dae57a3b648a
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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