Triethylamine → Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-cyano-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

HRID 2076659노트

반응식

HRID 2076659 반응식
C(N(CC)CC)C.CS(Cl)(=O)=O.[C:13]([O:17][C:18]([O:20][C:21]1[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[C:30]([CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]3[CH:51]=[CH:50][C:49]([CH2:52][C:53]([O:55][CH3:56])=[O:54])=[CH:48][C:47]=3[CH:57]=[N:58]O)=[CH:42][CH:41]=2)[C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19])([CH3:16])([CH3:15])[CH3:14]>ClCCl.C(OCC)(=O)C.C(O)C>[C:13]([O:17][C:18]([O:20][C:21]1[C:33]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:31]=[C:30]([CH2:38][O:39][C:40]2[CH:41]=[CH:42][C:43]([C:46]3[CH:51]=[CH:50][C:49]([CH2:52][C:53]([O:55][CH3:56])=[O:54])=[CH:48][C:47]=3[C:57]#[N:58])=[CH:44][CH:45]=2)[C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:19])([CH3:14])([CH3:15])[CH3:16]

참가 물질

7

반응물 3

HCID 8471Triethylamine2회HCID 31297Methanesulfonyl chlorideHCID 86617415Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-[(hydroxyimino)methyl]-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

생성물 1

HCID 67119222Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-cyano-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate수율 75.6%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Triethylamine (71 μl, 0.51 mmol) and methanesulfonyl chloride (23 μl, 0.31 mmol) were added to a solution of crude tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2′-[(hydroxyimino)methyl]-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (170 mg) obtained in the above in dichloromethane (4 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, successively washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. Triethylamine (71 μl, 0.51 mmol) was added to a solution of the obtained residue in ethanol (4 ml) and the mixture was heated under reflux for 14 hours. The solvent was removed under reduced pressure and the obtained residue was subjected to silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=2/1) to give crude tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2′-cyano-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (125 mg).

후처리

  1. washsuccessively washed with a saturated aqueous sodium hydrogencarbonate solution, water
  2. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 14 hours
  6. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-f7e74aba10ea468fb2b8b458b0b0bea7
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923573B2

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