Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:7])[C@@H:4]([CH3:6])[NH2:5].[CH2:8]1[CH2:14][S:11](=[O:13])(=[O:12])[O:10][CH2:9]1>C(#N)C>[CH3:1][O:2][C:3](=[O:7])[C@H:4]([NH:5][CH2:9][CH2:8][CH2:14][S:11]([OH:13])(=[O:12])=[O:10])[CH3:6]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of D-Alanine methylester (1.33 g, 12.9 mmol) in acetonitrile (15 mL was added 1,3-propane sultone (1.42 g, 11.7 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was filtered and washed with acetonitrile (2×15 mL). The solid was dissolved in water (30 mL). Dowex Marathon C ion exchange resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure and dried in vacuo, affording the title compound (1.52 g, 42%). 1H NMR (D2O, 500 MHz) δ ppm 4.07 (m, 1H), 3.72 (s, 3H), 3.14 (m, 2H), 2.89 (t, 2H, J=7.3 Hz), 2.03 (m, 2H), 1.46 (dd, 3H, J=1.95 Hz, 7.3 Hz). 13C (DMSO, 125 MHz) δ ppm 170.74, 55.62, 53.82, 47.96, 44.76, 21.53, 14.03. [α]D=+1.4° (c=0.0088 in water), ES-MS 224 (M−1).
Aufarbeitung
- temperatureat reflux for 2 hours
- filtrationThe solid material was filtered
- washwashed with acetonitrile (2×15 mL)
- dissolutionThe solid was dissolved in water (30 mL)
- additionDowex Marathon C ion exchange resin (strongly acidic) was added to the solution
- stirringThe suspension was stirred for 15 minutes before the resin
- customwas removed by filtration
- customThe filtrate was evaporated under reduced pressure
- customdried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-e0dfa5f28b2c4be09f62c0071fe6fda7
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08642801B2
Verknüpfte Notizen
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