Reaktionsgleichung
[NH2:1][CH2:2][CH2:3][CH2:4][P:5](=[O:8])([OH:7])[OH:6].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:27]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40]I)=[CH:38][CH:37]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].CCN(C(C)C)C(C)C.Cl>CO>[CH2:27]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH:1][CH2:2][CH2:3][CH2:4][P:5](=[O:7])([OH:6])[OH:8])=[CH:38][CH:37]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
3-Aminopropylphosphonic acid (0.060 g, 0.436 mmol) and tetrabutylammonium hydroxide (1.0M in methanol, 0.44 mL, 0.43 mmol) in methanol (3 mL) were heated at 50° C. for 15 min until all of the solids had dissolved. 4-(Nonyl)benzyliodide (0.100 g, 0.291 mmol) and DIEA (0.112 g, 0.872 mmol) were added and stirring was continued for 12 h at 50° C. The reaction was made acidic (pH˜5) by the addition of concentrated hydrochloric acid then directly purified using LC-3 to give the title compound (0.020 g): 1H NMR (500 MHz, CD3OD) δ 7.39 (d, J=8.0 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 4.15 (s, 2H), 3.14 (t, J=7.6 Hz, 2H), 2.64 (t, J=7.7 Hz, 2H), 2.00 (m, 2H), 1.79 (td, J=5.3, 18.5 Hz, 2H), 1.61 (m, 2H), 1.24-1.36 (m, 14H), 0.89 (t, J=7.0 Hz, 3H); ESI-MS 356.2 (M+H).
Aufarbeitung
- dissolutionhad dissolved
- customthen directly purified
Quellen und Nachweise
- ORD-Eintrag
- ord-7d43e672047d4628b071f11329423617
- Quelldatensatz
- uspto-grants-2008_04
- Patentnummer
- US07351725B2
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