Dimethylformamide → HCID 86658643, Verbindung

HRID 1625718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625718
[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]

Komponenten

6

Edukt 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, Verbindung

Produkt 1

HCID 86658643HCID 86658643, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-35e113e83fdb49b49c4f9626d18b6225
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785151B2

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