Acetone Cyanohydrin → 1,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(1-methylethyl)amino]butanoate
Reaktionsgleichung
[NH2:1][CH2:2][C@@H:3]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([Cl:21])[CH:14]=1)[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:22][C:23](C)(O)[C:24]#N>CCO>[Cl:21][C:15]1[CH:14]=[C:13]([NH:12][C@H:3]([CH2:2][NH:1][CH:23]([CH3:24])[CH3:22])[CH2:4][C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6])[CH:18]=[CH:17][C:16]=1[C:19]#[N:20]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A mixture of 1,1-dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate (0.309 g, 1 mmol), acetone cyanohydrin (0.1 g, 1.18 mmol) and crushed 4 Å molecular sieves in EtOH (5 mL) was stirred at 60° C. for 6 h. After cooled down, the reaction mixture was filtered. The filtrate was treated with NaBH4 (excess amount) and stirred for 2.5 h. The reaction was diluted with H2O and extracted with Et2O (2×). The organic extracts were washed with H2O (2×), dried over Na2SO4, filtered, and concentrated to yield the titled product (0.33 g, 94%). LC-MS (ES) m/e 352.5 (M+H)+.
Aufarbeitung
- temperatureAfter cooled down
- filtrationthe reaction mixture was filtered
- additionThe filtrate was treated with NaBH4 (excess amount)
- stirringstirred for 2.5 h
- additionThe reaction was diluted with H2O
- extractionextracted with Et2O (2×)
- washThe organic extracts were washed with H2O (2×)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-ea74e2e89dea42b4ab495bd56349f31b
- Quelldatensatz
- uspto-grants-2010_10
- Patentnummer
- US07816395B2
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