Tetrahydrofuran → HCID 178504281, Verbindung
Reaktionsgleichung
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].O1CCCC1.[NH2:18]/[C:19](=[N:36]\[OH:37])/[C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH2:22][CH2:21]1>ClCCl>[O:2]=[C:1]1[O:37][N:36]=[C:19]([C@H:20]2[CH2:21][CH2:22][C@H:23]([NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[CH2:24][CH2:25]2)[NH:18]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
Carbonyldiimidazole (1.24 g, 7.43 mmol) was added to a tetrahydrofuran (20 ml) solution of the compound (1.12 g, 3.71 mmol) obtained in Step 5 above under ice cooling and the resulting mixture was stirred at 50° C. for 24 hours. The reaction mixture was diluted with dichloromethane:methanol [10:1 (v/v)] and washed with 10% aqueous citric acid solution and saturated sodium bicarbonate solution in that order and then the organic layer was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→13:7→dichloromethane:methanol=49:1→19:1 (v/v)] to give 757 mg (62%) of the title compound as a colorless solid.
Aufarbeitung
- washmethanol [10:1 (v/v)] and washed with 10% aqueous citric acid solution and saturated sodium bicarbonate solution in that order
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- concentrationThe solvent was concentrated under reduced pressure
- customthe residue obtained
- customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→13:7→dichloromethane:methanol=49:1→19:1 (v/v)]
Quellen und Nachweise
- ORD-Eintrag
- ord-34b4ef73b0774e7fb6ac1d905a658440
- Quelldatensatz
- uspto-grants-2014_01
- Patentnummer
- US08629133B2
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