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

HRID 1919908
ノート
印刷プレビュー

反応式

HRID 1919908 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e838338f467b448bb4bb57b378844b99
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08168658B2

反応ノート

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