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Trifluoroacetic acid → 3-(Aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzamide

HRID 1889660
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HRID 1889660 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([Cl:35])[CH:34]=1)[CH2:5][N:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[C:7]([C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][NH:13]C(=O)OC(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:13][CH2:12][C:11]1[CH:10]=[C:9]([CH:23]=[CH:22][CH:21]=1)[C:7]([N:6]([CH2:5][C:4]1[CH:32]=[C:33]([Cl:35])[CH:34]=[C:2]([Cl:1])[CH:3]=1)[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)=[O:8]
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 66616567HCID 66616567, 화합물

생성물 1

HCID 585314683-(Aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzamide수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 3-((3,5-dichlorobenzyl)(4-fluorobenzyl)carbamoyl)benzylcarbamate (0.8 g, 1.55 mmol) in CH2Cl2 (8 mL) was added TFA (1.19 mL, 15.5 mmol). The reaction mixture was stirred at rt. for 4 h, concentrated and the residue was diluted with ethyl acetate and saturated aq NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give the product as a white solid (0.61 g, 95%). 1H NMR (DMSO-(d6): δ 7.52-7.06 (m, 11H), 4.65-4.40 (m, 4H), 3.72 (s, 2H); MS (ESI): [M+H]+=416.9.

후처리

  1. concentrationconcentrated
  2. additionthe residue was diluted with ethyl acetate and saturated aq NaHCO3 solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f394c57ac30849a6a3f0836c0f4b0f2e
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501992B2

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