Benzylacetylene → HCID 66579620, compound

HRID 1624385Notes

Reaction equation

HRID 1624385 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][N:28]=[N+:29]=[N-:30])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:31]1([CH2:37][C:38]#[CH:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][N:28]4[CH:39]=[C:38]([CH2:37][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[N:30]=[N:29]4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 575753BenzylacetyleneHCID 23667548Sodium AscorbateHCID 86652410HCID 86652410, compound

Product 1

HCID 66579620HCID 66579620, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 1-[4′-(4-azidomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.183 g, 0.45 mmol) in tBuOH (1.5 mL) and H2O (1.5 mL) was added 3-phenyl-1-propyne (0.053 g, 0.45 mmol), followed by sodium ascorbate (0.009 g, 0.045 mmol) and copper(II) sulfate pentahydrate (0.001 g, 0.005 mmol), and the reaction was stirred overnight. After aqueous workup, the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. customAfter aqueous workup, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-adb117a580a94432b1c10f43db4acc84
Source dataset
uspto-grants-2014_07
Patent number
US08778983B2

Reaction notes

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