Water → HCID 66579249, compound

HRID 1624412Notes

Reaction equation

HRID 1624412 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]([OH:17])[C:15]#[CH:16])=[CH:4][CH:3]=1.O.[N:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[N+:20]=[N-:21].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CS(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:22]([N:19]1[CH:16]=[C:15]([CH:14]([C:9]2[C:10]([CH3:13])=[N:11][O:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[OH:17])[N:21]=[N:20]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 866524111-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-prop-2-yn-1-ol

Product 1

HCID 66579249HCID 66579249, compound

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-prop-2-yn-1-ol (Enantiomer A) (0.530 g, 1.81 mmol) in DMSO (4 mL) and H2O (4 mL) was added azidomethyl-benzene (0.242 g, 1.81 mmol), followed by sodium ascorbate (0.036 g, 0.181 mmol) and copper(II) sulfate pentahydrate (0.005 g, 0.018 mmol), and the reaction was stirred overnight. After aqueous workup the crude material was purified by silica gel chromatography (15-100% EtOAc in hexanes) to give the title compound.

Workup

  1. customAfter aqueous workup the crude material was purified by silica gel chromatography (15-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-848de323e3424a3baf8bb54c3ac51736
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

Loading…