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

HRID 2076658노트

반응식

HRID 2076658 반응식
N1C=CC=CC=1.Cl.[NH2:8][OH:9].[C:10]([O:14][C:15]([O:17][C:18]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[C:27]([CH2:35][O:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][C:46]([CH2:49][C:50]([O:52][CH3:53])=[O:51])=[CH:45][C:44]=3[CH:54]=O)=[CH:39][CH:38]=2)[C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(O)C.C(OCC)(=O)C>[C:10]([O:14][C:15]([O:17][C:18]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[C:27]([CH2:35][O:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][C:46]([CH2:49][C:50]([O:52][CH3:53])=[O:51])=[CH:45][C:44]=3[CH:54]=[N:8][OH:9])=[CH:39][CH:38]=2)[C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16])([CH3:13])([CH3:12])[CH3:11]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86617414Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-formyl-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

생성물 1

HCID 86617415Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-[(hydroxyimino)methyl]-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate수율 83.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

Pyridine (49 μl, 0.62 mmol) and hydroxylamine hydrochloride (42 mg, 0.62 mmol) were added to a solution of tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2′-formyl-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (198 mg, 0.307 mmol) obtained in Example (45-2) in ethanol (4 ml), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate, successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure 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′-[(hydroxyimino)methyl]-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (170 mg).

후처리

  1. washsuccessively washed with water
  2. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  3. customThe residue obtained
  4. customby removing the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-aea64be630d74e6b88969e2ee64ef94a
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923573B2

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