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 2076658ノート

反応式

HRID 2076658 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aea64be630d74e6b88969e2ee64ef94a
出典データセット
uspto-grants-2011_04
特許番号
US07923573B2

反応ノート

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