Ethyl nitroacetate → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-2-nitro-propionic Acid Ethyl Ester

HRID 11697

반응식

HRID 11697 반응식
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][N+:6]([O-:8])=[O:7])[CH3:2].C(=O)(O)[O-].[Na+].[Cl:15][C:16]1[CH:41]=[CH:40][C:19]([O:20][CH2:21][C:22]([N:24]2[CH2:29][C@H:28]([CH3:30])[N:27]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH2:26][C@H:25]2[CH3:39])=[O:23])=[C:18]([CH2:42]Cl)[CH:17]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([N+:6]([O-:8])=[O:7])[CH2:42][C:18]1[CH:17]=[C:16]([Cl:15])[CH:41]=[CH:40][C:19]=1[O:20][CH2:21][C:22]([N:24]1[CH2:29][C@H:28]([CH3:30])[N:27]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[CH2:26][C@H:25]1[CH3:39])=[O:23])[CH3:2]

참가 물질

6

반응물 3

HCID 69379Ethyl nitroacetateHCID 516892Sodium BicarbonateHCID 234058422-[4-Chloro-2-(chloromethyl)phenoxy]-1-{(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl}ethan-1-one

생성물 1

HCID 865911673-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-2-nitro-propionic Acid Ethyl Ester수율 47%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To nitro-acetic acid ethyl ester (0.32 g, 2.39 mmol), sodium bicarbonate (0.10 g, 1.19 mmol) and tetrabutyl ammonium iodide (0.088 g, 0.24 mmol) in dimethyl formamide (5 ml) was added 2-(4-chloro-2-chloromethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.52 g, 1.19 mmol). After 1 hour of heating at 60° C. the reaction was concentrated and then diluted with methylene chloride. After washing with aqueous saturated sodium bicarbonate and saturated sodium chloride the organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.30 g).

후처리

  1. concentrationwas concentrated
  2. additiondiluted with methylene chloride
  3. washAfter washing with aqueous saturated sodium bicarbonate and saturated sodium chloride the organic layer
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-34e48198b45f4c59b72297ec362acb71
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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