Trifluoroacetic acid → 4-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid

HRID 1694831노트

반응식

HRID 1694831 반응식
[NH:1]([C:8](=[O:32])[CH:9]([C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]([C:8](=[O:32])[CH:9]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:30][CH:31]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59376446Tert-butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate

생성물 1

HCID 593764614-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate, prepared in the previous step, in CH2Cl2 (200 mL) at room temperature was added trifluoroacetic acid (50 mL). The reaction mixture was stirred at room temperature for 2 h and concentrated. The crude acid was dissolved in CH2Cl2, filtered, and precipitated with hexanes. The solid was collected by filtration, washed with hexanes, and dried under high vacuum to yield 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (7.58 g, 71% from dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate) as an off white solid: 1H NMR (600 MHz, DMSO-d6) δ 12.94 (s br, 1H), 10.26 (s br, 2H), 7.94 (d, J=8.2 Hz, 2H), 7.58 (d, J=7.6 Hz, 4H), 7.54 (d, J=8.2 Hz, 2H), 7.30 (t, J=7.6 Hz, 41-1), 7.05 (t, J=7.3 Hz, 2H), 4.97 (s, 1H); ESIMS calcd 375.1 (M++H), found 375.1 (M++H).

후처리

  1. concentrationconcentrated
  2. dissolutionThe crude acid was dissolved in CH2Cl2
  3. filtrationfiltered
  4. customprecipitated with hexanes
  5. filtrationThe solid was collected by filtration
  6. washwashed with hexanes
  7. customdried under high vacuum

출처 및 근거

ORD 기록
ord-c0be64cf18e547d8812e4f5e53db3d4d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158825B2

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