Water → HCID 66579249, compound

HRID 1183343Notes

Reaction equation

HRID 1183343 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-8012bcf7b6e74261b6e9478d1897c6a8
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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