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

HRID 1480393Notes

Reaction equation

HRID 1480393 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:18])(=[O:17])[CH2:12][CH2:13][CH2:14][C:15]#[CH:16].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:16]=[C:15]([CH2:14][CH2:13][CH2:12][C:11]([OH:18])=[O:17])[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 1430365-Hexynoic acidHCID 23667548Sodium Ascorbate

Product 1

HCID 247519584-(1-Benzyl-1H-1,2,3-triazol-4-yl)butanoic 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). Hex-5-ynoic acid (2.337 ml, 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 for 72 hrs. Sodium chloride (solid) was added to the reaction mixture followed by EtOAc (100 ml). The phases separated and the aqueous layer was further extracted with EtOAc. The organics phases were combined, dried over MgSO4 (anh), filtered and evaporated under reduced pressure 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

Sources & evidence

ORD record
ord-6fc92399e9174cb4b87bdf2a92028df8
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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