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

HRID 1269617노트

반응식

HRID 1269617 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4c6068d9093c47a6a4fe3a221c55ad1d
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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