Hydrochloric Acid → 3-{4-[4-(2,4,6-Trimethylphenyl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804163

반응식

HRID 1804163 반응식
[O:1]=[C:2]1[N:6]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=O)=[CH:9][CH:8]=2)[CH2:5][CH2:4][O:3]1.[OH-].[Na+].Cl.[CH3:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:23]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C(O)C>[CH3:29][C:24]1[CH:25]=[C:26]([CH3:28])[CH:27]=[C:22]([CH3:21])[C:23]=1[N:30]1[CH2:31][CH2:32][N:33]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([N:6]3[CH2:5][CH2:4][O:3][C:2]3=[O:1])=[CH:17][CH:16]=2)=[O:13])[CH2:34][CH2:35]1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 616604Ethyl p-(2-oxo-1,3-oxazolidin-3-yl)benzoateHCID 27608221-(2,4,6-Trimethylphenyl)piperazineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate

생성물 1

HCID 674473683-{4-[4-(2,4,6-Trimethylphenyl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one수율 9.6%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
50 °C

실험 절차

To ethyl 4-(-2-oxooxazolidin-3-yl)benzoate (0.235 g) described in Preparation Example 12 were added 1 M aqueous sodium hydroxide solution (1.3 mL) and ethanol (5 mL), and the mixture was stirred at 50° C. 1N hydrochloric acid (1.3 mL) was added, 1-(2,4,6-trimethylphenyl)piperazine (0.215 g) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (0.277 g) were added, and the mixture was stirred at room temperature overnight. The mixture was extracted with ethyl acetate, washed with saturated brine, and the solvent was evaporated. The residue was purified by HPLC (ODS, 0.05% TFA aqueous solution-acetonitrile) to give the title compound (37.7 mg).

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. customthe solvent was evaporated
  5. customThe residue was purified by HPLC (ODS, 0.05% TFA aqueous solution-acetonitrile)

출처 및 근거

ORD 기록
ord-540f18ada2da4cee81800e4aebeff0b0
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354401B2

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