Sodium Chloride → 3-(1-Benzyl-1H-1,2,3-triazol-4-yl)propanoic acid

HRID 1480399Notes

Reaction equation

HRID 1480399 reaction equation
[CH2:1]([N:8]=[N+:9]=[N-:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([OH:17])(=[O:16])[CH2:12][CH2:13][C:14]#[CH:15].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[Cl-].[Na+]>C(O)(C)(C)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CCOC(C)=O>[CH2:1]([N:8]1[CH:15]=[C:14]([CH2:13][CH2:12][C:11]([OH:17])=[O:16])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 12152Benzyl azideHCID 224644-Pentynoic acidHCID 23667548Sodium Ascorbate

Product 1

HCID 247519593-(1-Benzyl-1H-1,2,3-triazol-4-yl)propanoic acid

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl azide (2.82 ml, 21.18 mmol) was dissolved in tert-butanol (212 ml) and water (212 ml). Pent-4-ynoic acid (2.078 g, 21.18 mmol) was added followed by copper (II) acetate (385 mg, 2.118 mmol) and sodium L-ascorbate (837 mg, 4.24 mmol) and the reaction mixture was stirred vigorously overnight. Sodium chloride (solid) was added to the reaction mixture followed by EtOAc. The phases separated and the aqueous layer was further extracted with EtOAc. The organic phases were combined, dried over MgSO4 (anh), filtered and evaporated under reduced pressure and dried in a vacuum oven to afford the title compound;

Workup

  1. customThe phases separated
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. dry with materialdried over MgSO4 (anh)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-160f397b732e405c987f3b3de75cd7de
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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