Reaktionsgleichung
Cl.[C:2]1([CH:8]([C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=[O:12])[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:18]([CH2:21][CH3:22])CC)C.CN([CH:26]=[O:27])C>>[C:21]([C:22]1[CH:6]=[CH:7][C:2]([C:26]([NH:9][CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=[O:12])=[O:27])=[CH:3][CH:4]=1)#[N:18]Komponenten
Versuchsvorschrift
β-Phenyl-α,α-dimethyl-β-alanine hydrochloride (1.88 g, 8.19 mmol) was dissolved in DMF (100 ml). To the resulting solution, triethylamine (Et3N) (3.5 ml, 25.11 mmol) and 4-cyanobenzoyl-N-hydroxysuccinimide ester (4-cyanobenzoyl-OSu) (2.2 g, 9.01 mmol) were added under cooling with ice and the mixture was stirred at room temperature overnight. The solvent was distilled off and the residue was dissolved in a 5% aqueous ammonia and washed with ether. The aqueous layer was adjusted to pH 3 with citric acid under cooling with ice and extracted with ethyl acetate. The collected ethyl acetate layer was washed with a saturated aqueous solution of NaCl and dried over anhydrous sodium sulfate. The solvent was distilled off and a crystal of N-4-cyanobenzoyl-β-phenyl-α,α-dimethyl-β-alanine was obtained upon recrystallization from an ether-hexane mixed solution (2.54 g, 96.2%).
Aufarbeitung
- temperatureunder cooling with ice
- distillationThe solvent was distilled off
- dissolutionthe residue was dissolved in a 5% aqueous ammonia
- washwashed with ether
- temperatureunder cooling with ice
- extractionextracted with ethyl acetate
- washThe collected ethyl acetate layer was washed with a saturated aqueous solution of NaCl
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off
Quellen und Nachweise
- ORD-Eintrag
- ord-ae7674cf9d31416e96daefa51333a4d8
- Quelldatensatz
- uspto-grants-1999_02
- Patentnummer
- US05866592
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