1-(2-Methoxymethoxyphenyl)-5,5-dimethylpiperazin-2-one → N-{(S)-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]-2-[4-(2-methoxymethoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1694910Notes

Reaction equation

HRID 1694910 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][O:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:35]1[CH2:40][C:39]([CH3:42])([CH3:41])[NH:38][CH2:37][C:36]1=[O:43]>C1(C)C=CC=CC=1>[CH:1]([C@H:4]1[C:5](=[O:24])[O:6][C@H:7]([C@@H:9]([NH:10][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])[CH2:11][N:38]2[CH2:37][C:36](=[O:43])[N:35]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[O:28][CH2:27][O:26][CH3:25])[CH2:40][C:39]2([CH3:42])[CH3:41])[CH2:8]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 666456561-(2-Methoxymethoxyphenyl)-5,5-dimethylpiperazin-2-oneHCID 178448140HCID 178448140, compound

Product 1

HCID 66645812N-{(S)-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]-2-[4-(2-methoxymethoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]ethyl}-2-nitrobenzenesulfonamideYield 87.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 214 mg of (3S,5S)-3-isopropyl-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]dihydrofuran-2-one obtained in Example (1g) (0.60 mmol) and 207 mg of 1-(2-methoxymethoxyphenyl)-5,5-dimethylpiperazin-2-one obtained in Example (12a) (0.78 mmol) in toluene (7 ml) was stirred at 110° C. for 45 minutes. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=20/1) to obtain 326 mg of N-{(S)-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]-2-[4-(2-methoxymethoxyphenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]ethyl}-2-nitrobenzenesulfonamide (yield: 87%).

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/methanol=20/1)

Sources & evidence

ORD record
ord-73d0ad4bfbc143dd9d840cc833483689
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

Loading…