Acetic Acid → Ethyl [2-methyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate

HRID 1269617ノート

反応式

HRID 1269617 の反応式
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)=O.[F:17][C:18]([F:33])([F:32])[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=2)=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH3:16][C:5]1[CH:4]=[C:3]([CH2:1][NH:31][C:27]2[CH:26]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:32])[F:33])=[CH:20][CH:21]=3)[CH:30]=[CH:29][CH:28]=2)[CH:15]=[CH:14][C:6]=1[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 27827084'-(Trifluoromethyl)-[1,1'-biphenyl]-3-amineHCID 5049666Sodium triacetoxyborohydrideHCID 58622891Ethyl (4-formyl-2-methylphenoxy)acetate

生成物 1

HCID 58622902Ethyl [2-methyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate収率 85.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of ethyl (4-formyl-2-methylphenoxy)acetate (0.2 g, 0.9 mmol) in anhydrous CH2Cl2 (8 mL) was added 4′-(trifluoromethyl)-1,1′-biphenyl-3-ylamine (0.214 g, 0.9 mmol). The resulting mixture was stirred under nitrogen at room temperature for 15 mins, prior to addition of sodium triacetoxyborohydride (0.267 g, 1.26 mmol) and acetic acid (0.052 mL, 0.9 mmol). The resultant mixture was stirred for 18 h prior to quenching by cautious addition of sat. sodium bicarbonate solution (20 mL) the reaction mixture was then extracted CH2Cl2 (20 mL). The organic extract separated by hydrophobic frit and the solvent removed in vacuo. Purification by Biotage™ chromatography (Silica, 40 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (0.342 g).

後処理

  1. customto quenching by cautious addition of sat. sodium bicarbonate solution (20 mL) the reaction mixture
  2. extractionThe organic extract
  3. customseparated by hydrophobic frit
  4. customthe solvent removed in vacuo
  5. customPurification by Biotage™ chromatography (Silica, 40 g)
  6. washeluting 9:1 cyclohexane

出典と根拠

ORDレコード
ord-4c6068d9093c47a6a4fe3a221c55ad1d
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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