Sodium Carbonate → Tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methoxy]quinolin-3-yl}methyl)carbamate

HRID 1986464노트

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HRID 1986464 반응식
[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:8]2[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)#[N:2].[Cl-].O[NH3+].[C:38](=[O:41])([O-])[O-:39].[Na+].[Na+].C(N1C=CN=C1)([N:46]1C=CN=C1)=O>O.C(O)C>[CH2:15]([C:10]1[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:8]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH2:3][C:1]3[NH:46][C:38](=[O:41])[O:39][N:2]=3)[CH:6]=2)[N:11]=1)[CH:16]([CH3:17])[CH3:18]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 21645Hydroxylamine HClHCID 682631,1'-CarbonyldiimidazoleHCID 86605640Tert-butyl {[6-(cyanomethoxy)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

생성물 1

HCID 136385126Tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methoxy]quinolin-3-yl}methyl)carbamate수율 35%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

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온도
70 °C

실험 절차

A mixture of tert-butyl {[6-(cyanomethoxy)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.46 g, 1.0 mmol), hydroxyammonium chloride (0.21 g, 3.0 mmol), sodium carbonate (0.43 g, 4.0 mmol) and ethanol (10 ml) was stirred at 70° C. for 17 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 ml). 1,1′-Carbonylbis-1H-imidazole (0.32 g, 2.0 mmol) was added and the mixture was stirred at 70° C. for 24 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methoxy]quinolin-3-yl}methyl)carbamate (0.18 g, yield 35%) as pale-yellow crystals.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (10 ml)
  6. stirringthe mixture was stirred at 70° C. for 24 hrs
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1b065cf9c3ca4bb797ff697fdde62bdc
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547710B2

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