Aniline → Tert-butyl 4-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoate

HRID 1919905ノート

反応式

HRID 1919905 の反応式
[C:1]([NH:4][CH2:5][CH:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:12][CH:11]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].CCN=C=NCCCN(C)C.[CH:34]1[CH:35]=[CH:36][C:37]2N(O)N=[N:40][C:38]=2[CH:39]=1.NC1C=CC=CC=1>CN(C=O)C>[C:1]([NH:4][CH2:5][CH:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:12][CH:11]=1)[C:7]([NH:40][C:38]1[CH:39]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:9])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 576119543-(Acetylamino)-2-[4-(tert-butoxycarbonyl)phenyl]propanoic acid

生成物 1

HCID 57611876Tert-butyl 4-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-(Acetylamino)-2-[4-(tert-butoxycarbonyl)phenyl]propanoic acid (222 mg, 0.72 mmol), EDCI (207 mg, 1.08 mmol), and HOBT (127 mg, 0.94 mmol) were dissolved in DMF (7 mL) and stirred for 5 minutes before adding aniline (99 μL, 1.08 mmol). After stirring at room temperature for 18 h, the solution was concentrated. The resulting residue was taken up in EtOAc, washed (water, sat. NaHCO3, brine), dried (MgSO4), and concentrated. Flash chromatography on silica (0-4% MeOH/DCM) afforded tert-butyl 4-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoate as an off-white solid. 1H NMR (DMSO-d6) δ10.18 (s, 1H), 8.08 (t, J=5.9 Hz, 1H), 7.84 (d, J=8.5 Hz, 2H), 7.56 (d, J=7.6 Hz, 2H), 7.46 (d, j=8.2 Hz, 2H), 7.25 (t, J=7.9 Hz, 2H), 7.00 (t, J=7.5 Hz, 1H), 4.03 (dd, J=8.2, 6.3 Hz, 1H), 3.51 (ddd, J=13.2, 8.4, 5.0 Hz, 1H), 3.42 (dt, J=12.9, 6.5 Hz, 1H), 1.74 (s, 3H), 1.50 (s, 9H). MS (ESI) calcd [M+H]+ 383.2, found 383.1.

後処理

  1. stirringAfter stirring at room temperature for 18 h
  2. concentrationthe solution was concentrated
  3. washwashed (water, sat. NaHCO3, brine)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8028ca5bb3474fec9e002576e77d7e17
出典データセット
uspto-grants-2012_05
特許番号
US08168658B2

反応ノート

読み込み中…