Isopropylamine → Esatenolol
Reaktionsgleichung
[C:1]([CH2:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][CH:11]2[O:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:3])[NH2:2].[CH:16]([NH2:19])([CH3:18])[CH3:17]>CO>[CH3:17][CH:16]([NH:19][CH2:12][C@H:11]([OH:13])[CH2:10][O:9][C:8]1[CH:14]=[CH:15][C:5]([CH2:4][C:1]([NH2:2])=[O:3])=[CH:6][CH:7]=1)[CH3:18]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 10 °C
Versuchsvorschrift
P-Hydroxyphenylacetamide (1 g) and (S)-glycidyl p-toluenesulfonate (1.51 g, 99.3% e.e.) were dissolved in acetone (30 ml). Potassium carbonate (1.19 g) was added to the solution and stirred for 30 hours under refluxing. After the reaction, inorganic materials were filtered off and acetone was removed to give 1.43 g of crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane. Then, crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane (1.43 g) was dissolved in methanol (8 ml). The solution was dropped in isopropylamine (6.8 g) under cooling to 10° C. over a period of 1 hour and the reaction temperature was raised to room temperature and stirred for 7 hours. After the reaction, the mixture was condensed in vacuo until crystals beginning to separate, cooled, filtrated by suction and dried in vacuo to give crude (S)-atenolol (1.29 g). The optical purity of it was 62.8% e.e. by measurement of Chiral column OD (Daisel Chemical industries Ltd.).
Aufarbeitung
- temperaturethe reaction temperature was raised to room temperature
- customAfter the reaction
- customcondensed in vacuo until crystals
- customto separate
- temperaturecooled
- filtrationfiltrated by suction
- customdried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-8489f136fb044bed8b4bbc3ff88869ab
- Quelldatensatz
- uspto-grants-2000_05
- Patentnummer
- US06057476
Notizen zur Reaktion
Wird geladen…