Oxalic Acid → (2R)-1-(3'-(Methoxycarbonyl)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol oxalic acid salt

HRID 1600967노트

반응식

HRID 1600967 반응식
S(=O)(=O)(O)O.[C:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]([OH:32])[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)([OH:8])=[O:7].[C:33](=O)([O-])O.[Na+].[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40]>CO.CCOCC>[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40].[CH3:33][O:7][C:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C@H:23]([OH:32])[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)=[O:8]

참가 물질

7

반응물 4

HCID 971Oxalic AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 54073875(2R)-1-(3'-Carboxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

생성물 1

HCID 67597801(2R)-1-(3'-(Methoxycarbonyl)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol oxalic acid salt

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

Concentrated sulfuric acid (2.5 ml) was added to a suspension of (2R)-1-(3'-carboxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol (0.5 g) in methanol (50 ml). The mixture was heated at reflux for 10 hours. The mixture was cooled to room temperature and made basic by addition of aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:methanol (19:1) to give an oil which was converted to the oxalate salt upon treatment with oxalic acid (excess) in ether to give the title compound as a solid (0.482 g).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with dichloromethane:methanol (19:1)
  8. customto give an oil which

출처 및 근거

ORD 기록
ord-32e69279272a4c80baf9bc4bca78ad28
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977105

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