Trifluoroacetic acid → (R)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamine

HRID 1582809노트

반응식

HRID 1582809 반응식
FC(F)(F)C(O)=O.C(OC([NH:15][C@H:16]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:36][CH:35]=1)[CH2:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:20]=1[Br:33])=O)(C)(C)C.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[CH2:26]([O:25][C:23]1[CH:22]=[CH:21][C:20]([Br:33])=[C:19]([CH:24]=1)[O:18][CH2:17][C@H:16]([NH2:15])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:36][CH:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 21226206Ethyl acetate hexaneHCID 60086347(R)-N-(tert-butoxycarbonyl)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamine

생성물 1

HCID 60086312(R)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamine수율 76.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (1 ml) was added to (R)-N-(tert-butoxycarbonyl)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamine (200 mg, 0.331 mmol) in methylene chloride (1 ml), followed by stirring for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, made basic with saturated aqueous sodium bicarbonate, and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=2/1, v/v) to give (R)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamine (127 mg, Yield 76%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent

출처 및 근거

ORD 기록
ord-aeeebf23906f4f6ab6c26ae86b844e34
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737417B2

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