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Trifluoroacetic acid → 4-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}-N-[2-amino-5-(3-thienyl)phenyl]benzamide

HRID 1919908
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HRID 1919908 반응식
[C:1]([NH:4][CH2:5][CH:6]([C:16]1[CH:43]=[CH:42][C:19]([C:20]([NH:22][C:23]2[CH:28]=[C:27]([C:29]3[CH:33]=[CH:32][S:31][CH:30]=3)[CH:26]=[CH:25][C:24]=2[NH:34]C(=O)OC(C)(C)C)=[O:21])=[CH:18][CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8])(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[C:1]([NH:4][CH2:5][CH:6]([C:16]1[CH:43]=[CH:42][C:19]([C:20]([NH:22][C:23]2[CH:28]=[C:27]([C:29]3[CH:33]=[CH:32][S:31][CH:30]=3)[CH:26]=[CH:25][C:24]=2[NH2:34])=[O:21])=[CH:18][CH:17]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:8])(=[O:3])[CH3:2]
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참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57611920Tert-butyl [2-[(4-{[(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoyl)amino]-4-(3-thienyl)phenyl]carbamate

생성물 1

HCID 576118554-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}-N-[2-amino-5-(3-thienyl)phenyl]benzamide

시약·촉매·용매 2

HCID 6344Dichloromethane
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of tert-butyl [2-[(4-{1 [(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoyl)amino]-4-(3-thienyl)phenyl]carbamate (164 mg, 0.27 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (2 mL), and the reaction was stirred at room temperature for 2 h. Concentration yielded a yellow residue that was dissolved in EtOAc, neutralized with sat. NaHCO3, washed with brine, dried (MgSO4), and evaporated. The resulting solid was dissolved in CH2Cl2 (15 mL) and MeOH (0.5 mL). Hexanes (5 mL) were added, and upon concentration to half-volume, the mixture was filtered to isolate 4-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}-N-[2-amino-5-(3-thienyl)phenyl]benzamide as a white solid. 1H NMR (DMSO-d6) δ10.19 (s, 1H), 9.66 (s, 1H), 8.12 (t, J=5.7 Hz, 1H), 7.95 (d, J=8.2 Hz, 2H), 7.58 (d, J=7.6 Hz, 2H), 7.54-7.52 (m, 2H), 7.49-7.47 (m, 3H), 7.38 (dd, J=4.7, 1.5 Hz, 1H), 7.33 (dd, J=8.2, 2.1 Hz, 1H), 7.26 (t, J=7.9 Hz, 2H), 7.01 (t, J=7.5 Hz, 1H), 6.78 (d, J=8.5 Hz, 1H), 4.99 (s, 2H), 4.06 (dd, J=8.5, 6.2 Hz, 1H), 3.54 (ddd, J=13.3, 8.5, 5.0 Hz, 1H), 3.47 (dt, J=12.9, 6.2 Hz, 1H), 1.76 (s, 3H). MS (ESI) calcd [M+H]+ 499.1, found 499.1.

후처리

  1. concentrationConcentration
  2. customyielded a yellow residue that
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe resulting solid was dissolved in CH2Cl2 (15 mL)
  7. additionHexanes (5 mL) were added
  8. concentrationupon concentration to half-volume
  9. filtrationthe mixture was filtered

출처 및 근거

ORD 기록
ord-e838338f467b448bb4bb57b378844b99
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08168658B2

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