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,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1694945Notes

Reaction equation

HRID 1694945 reaction equation
[CH:1]([C@@H:4]1[CH2:8][C@@H:7]([CH:9]2[CH2:11][N@@:10]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[O:6][C:5]1=[O:24])([CH3:3])[CH3:2].[CH3:25][C:26]1([CH3:41])[CH2:31][N:30]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[CH3:39])[C:29](=[O:40])[CH2:28][NH:27]1>C1(C)C=CC=CC=1>[CH3:25][C:26]1([CH3:41])[CH2:31][N:30]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[CH3:39])[C:29](=[O:40])[CH2:28][N:27]1[CH2:11][C@H:9]([NH:10][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[C@@H:7]1[CH2:8][C@@H:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:24])[O:6]1

Participants

4

Reactant 2

HCID 666457455,5-Dimethyl-1-(5-fluoro-2-methylphenyl)piperazin-2-oneHCID 178448140HCID 178448140, compound

Product 1

HCID 66645703N-{(S)-2-[2,2-Dimethyl-4-(5-fluoro-2-methylphenyl)-5-oxopiperazin-1-yl]-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 100.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 863 mg of (3S,5S)-3-isopropyl-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]dihydrofuran-2-one obtained in Example (1g) (2.43 mmol) and 805 mg of 5,5-dimethyl-1-(5-fluoro-2-methylphenyl)piperazin-2-one obtained in Example (70d) (3.40 mmol) in toluene (30 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=5/1-3/1) to obtain 1.44 g of the title compound (yield: 99%).

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=5/1-3/1)

Sources & evidence

ORD record
ord-075244b38f7947f192be60f0a1f04285
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

Loading…