Captopril → HCID 86595500, Verbindung
Reaktionsgleichung
[CH3:1][C@@H:2]([C:5]([N:7]1[C@H:11]([C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8]1)=[O:6])[CH2:3][SH:4].C(N(CC)C(C)C)(C)C.[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](Cl)=[O:31]>O.CC#N>[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]([S:4][CH2:3][C@@H:2]([CH3:1])[C:5]([N:7]1[CH2:8][CH2:9][CH2:10][C@H:11]1[C:12]([OH:14])=[O:13])=[O:6])=[O:31]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Captopril (3.50 g, 0.0161 Mol) and N,N-diisopropyl ethylamine (6.80 ml, 0.039 Mol) were dissolved in H2O/CH3CN (80 ml, 1:1) and the mixture was cooled to 0° C. Then 4-chlorobutylchloroformate (2.70 ml, 0.0198 Mol) was added and the reaction was slowly warmed to room temperature and stirred for 4 h. The mixture was then partitioned between HCl (4%, 100 ml) and EtOAc (100 ml). The organic layer was separated and the aqueous phase was extracted with EtOAc (2×100 ml). The combined organic phases were washed with brine (3×60 ml), dried over sodium sulphate and evaporated under reduced pressure affording 1-[(2S)-3-(4-chlorobutoxycarbonyl)mercapto-2-methyl-1-oxopropyl]-L-proline (5.90 g) as a colourless oil that was used without further purification.
Aufarbeitung
- temperaturethe reaction was slowly warmed to room temperature
- customThe mixture was then partitioned between HCl (4%, 100 ml) and EtOAc (100 ml)
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with EtOAc (2×100 ml)
- washThe combined organic phases were washed with brine (3×60 ml)
- dry with materialdried over sodium sulphate
- customevaporated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-9c8771c4d9494f3c905492d2cd2812fd
- Quelldatensatz
- uspto-grants-2007_01
- Patentnummer
- US07169805B2
Notizen zur Reaktion
Wird geladen…