Reaktionsgleichung
[CH3:1][C:2](=[CH2:21])[C:3](=[O:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][CH:6]1[CH2:10][CH2:9][NH:8][C:7]1=[O:11].[OH:22]O.C(#N)C1C=CC=CC=1.CCN(C(C)C)C(C)C>CO.O>[CH3:21][C@:2]1([C:3](=[O:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:5][CH:6]2[CH2:10][CH2:9][NH:8][C:7]2=[O:11])[CH2:1][O:22]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of tert-butyl ((2S)-4-methyl-3-oxo-1-(2-oxopyrrolidin-3-yl)pent-4-en-2-yl)carbamate (200 mg, 0.67 mmol) in methanol (10 mL) at 0° C. was added 30% H2O2 (1.5 g, 1.4 mmol) followed by addition of benzonitrile (520 mg, 5.00 mmol) and DIPEA (0.87 mL, 5.0 mmol). The reaction mixture was stirred for 8 h at ambient temperature and then diluted with water (25 mL). The resulting mixture was extracted with EtOAc (50 mL×2). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (heptanes/EtOAc=2:1) to afford tert-butyl ((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-(-2-oxopyrrolidin-3-yl) propan-2-yl)carbamate (95 mg, 45% yield) as a yellow oil.
Aufarbeitung
- extractionThe resulting mixture was extracted with EtOAc (50 mL×2)
- washThe combined extracts were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was purified by flash column chromatography on silica gel (heptanes/EtOAc=2:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-fc8f2252f41a45e78bee8d8c1ed7f2bc
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09434761B2
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