5,5-Dimethyl-1-(5-fluoro-2-methylphenyl)piperazin-2-one → N-{(S)-2-[2,2-Dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1694979Notes

Reaction equation

HRID 1694979 reaction equation
[CH3:1][C@@H:2]1[CH2:6][C@@H:5]([CH:7]2[CH2:9][N@@:8]2[S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[O:4][C:3]1=[O:22].[CH3:23][C:24]1([CH3:39])[CH2:29][N:28]([C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[CH3:37])[C:27](=[O:38])[CH2:26][NH:25]1>C1(C)C=CC=CC=1>[CH3:23][C:24]1([CH3:39])[CH2:29][N:28]([C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[CH3:37])[C:27](=[O:38])[CH2:26][N:25]1[CH2:9][C@H:7]([NH:8][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C@@H:5]1[CH2:6][C@@H:2]([CH3:1])[C:3](=[O:22])[O:4]1

Participants

4

Reactant 2

HCID 666457455,5-Dimethyl-1-(5-fluoro-2-methylphenyl)piperazin-2-oneHCID 178461437HCID 178461437, compound

Product 1

HCID 66645558N-{(S)-2-[2,2-Dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 844 mg of (3R,5S)-3-methyl-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]dihydrofuran-2-one obtained in Example (76g) (2.59 mmol) and 733 mg of 5,5-dimethyl-1-(5-fluoro-2-methylphenyl)piperazin-2-one obtained in Example (70d) (3.10 mmol) in toluene (26 ml) was stirred at 110° C. for two hours. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/ethyl acetate=3/1-1/1) to obtain 1.39 g of the title compound (yield: 95%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/ethyl acetate=3/1-1/1)

Sources & evidence

ORD record
ord-aea4ac50093c4fe3827d7b121b1c3f9a
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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