Ammonia → HCID 66992715, compound

HRID 1855659Notes

Reaction equation

HRID 1855659 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15])[CH2:2][C:3]#[CH:4].[N:16]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[N+:17]=[N-:18].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].N>[O-]S([O-])(=O)=O.[Cu+2].O.C(O)(C)(C)C>[O:15]=[C:6]1[C:7]2[C:8](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:10])[N:5]1[CH2:1][CH2:2][C:3]1[N:18]=[N:17][N:16]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:24])([CH3:23])[CH3:25])[CH:4]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 11171619N-(3-Butynyl)phthalimideHCID 11521126Azidomethyl 2,2-dimethylpropanoateHCID 23667548Sodium Ascorbate

Product 1

HCID 66992715HCID 66992715, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

702 mg (3.52 mmol) of N-(3-butynyl)phthalimide and 552 mg (3.51 mmol) of 2,2-dimethylpropionic acid azidomethyl ester are suspended in a water/t-butanol mixture (1/1, 10.5 ml). 0.18 ml of a 1M CuSO4 solution is added. 206 mg (1.04 mmol) of sodium ascorbate are then added. After 4 hours, the reaction is stopped by adding aqueous ammonia solution, and the reaction medium is extracted with EtOAc. The organic phase is then washed with brine and dried over MgSO4, filtered and concentrated. 1.11 g of 2,2-dimethylpropionic acid 4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,3]triazol-1-ylmethyl ester in the form of a yellow oil are obtained in a yield of 88%.

Workup

  1. extractionthe reaction medium is extracted with EtOAc
  2. washThe organic phase is then washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-634846915d2e4c88a8c2394150baeb96
Source dataset
uspto-grants-2015_02
Patent number
US08962846B2

Reaction notes

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