HCID 22390712, compound → HCID 57932476, compound

HRID 1432024Notes

Reaction equation

HRID 1432024 reaction equation
[CH2:1]([C@H:4]1[N:9]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:8][CH2:7][NH:6][C:5]1=[O:20])[C:2]#[CH:3].[N:21]([CH2:24][CH2:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1)=[N+:22]=[N-:23]>O1CCOCC1.CC(O)(C)C.O.CCOC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[O:20]=[C:5]1[NH:6][CH2:7][CH2:8][N:9]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C@@H:4]1[CH2:1][C:2]1[N:23]=[N:22][N:21]([CH2:24][CH2:25][C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=2)[CH:3]=1

Participants

8

Reactant 2

HCID 22390712HCID 22390712, compoundHCID 86604870HCID 86604870, compound

Product 1

HCID 57932476HCID 57932476, compound

Reagents, catalysts & solvents 5

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-3-(prop-2-ynyl)-4-tosylpiperazin-2-one (292 mg, 1 mmol) and 4-(2-azidoethyl)benzonitrile (172 mg, 1 mmol) in dioxane (3 mL) and t-BuOH (4 mL) was added a solution of copper(2+) sulfate, pentahydrate (249 mg, 1 mmol) in 0.5 mL of water, followed with a solution of (+)-sodium 1-ascorbate (198 mg, 1 mmol) in 0.5 mL of water. The resulting solution was stirred at room temperature for 2 h. The reaction was diluted with EtOAc, washed with brine, dried over Na2SO4, and evaporated to dryness. Flash chromatography (SiO2, EtOAc to EtOAc/MeOH=100:10 to 100:15) afforded the title compound as a white solid.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-07ca05b2b97a4481a879d2b12381e166
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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