Dimethylformamide → HCID 86658643、化合物

HRID 1625718ノート

反応式

HRID 1625718 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]=[O:16])[O:5][CH2:6][CH2:7][CH2:8][C:9]([O-:11])=O.[Li+].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.[N+:47]([C:50]1[CH:55]=[C:54]([N+:56]([O-:58])=[O:57])[CH:53]=[CH:52][C:51]=1[NH:59][CH2:60][CH2:61][NH2:62])([O-:49])=[O:48]>CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]=[O:16])[O:5][CH2:6][CH2:7][CH2:8][C:9]([NH:62][CH2:61][CH2:60][NH:59][C:51]1[CH:52]=[CH:53][C:54]([N+:56]([O-:58])=[O:57])=[CH:55][C:50]=1[N+:47]([O-:49])=[O:48])=[O:11]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 168833(2,4-Dinitrophenyl)ethylenediamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58481206HCID 58481206、化合物

生成物 1

HCID 86658643HCID 86658643、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Lithium 4-(3-amino-4-formylphenoxy)butanoate (50 mg), HBTU (80 mg) and DMF (2 mL) were combined in a 20 mL glass vial and stirred at ambient temperature. After 30 minutes, N1-(2,4-dinitrophenyl)ethane-1,2-diamine (Oakwood, 45 mg) was added in one portion and the reaction was stirred at ambient temperature overnight. The reaction mixture was diluted with EtOAc, washed successively with dilute aq. citric acid, water, sat. aq.NaHCO3, water, and sat. aq.NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure, affording the title compound as a yellow solid. Rf: 0.18 (SiO2, EtOAc). MS (ESI+): m/z 432.20 (MH+). H-NMR (400 MHz, DMSO-d6): 1.914 (2H, quint, J=7.0 Hz), 2.224 (2H, t, J=7.0 Hz), 3.349 (2H, q, J=6.0 Hz), 3.538 (2H, q, J=6.0 Hz), 3.928 (2H, t, J=6.4 Hz), 6.165 (1H, s), 6.176 (1H, dd, J=2.4, 10.0 Hz), 7.133 (1H, br.s), 7.268 (1H, d, J=10.0 Hz), 7.371 (1H, d, J=8.4 Hz), 8.167 (1H, t, J=5.8 Hz), 8.250 (1H, dd, J=2.8, 8.8 Hz), 8.835 (1H, d, J=2.8 Hz), 8.913 (1H, t, J=5.6 Hz), 9.599 (1H, s). C-NMR (100 MHz, DMSO-d6): 24.489, 31.436, 37.331, 42.745, 66.782, 98.040, 104.339, 112.751, 115.130, 123.472, 123.564, 129.725, 134.731, 137.484, 148.305, 152.824, 163.873, 172.251, 191.400.

後処理

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. washwashed successively with dilute aq. citric acid, water
  3. dry with materialNaCl, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-35e113e83fdb49b49c4f9626d18b6225
出典データセット
uspto-grants-2014_07
特許番号
US08785151B2

反応ノート

読み込み中…