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

HRID 2076659ノート

反応式

HRID 2076659 の反応式
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]

参加物

7

反応物 3

HCID 8471Triethylamine2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f7e74aba10ea468fb2b8b458b0b0bea7
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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