Reaktionsgleichung
[CH3:1][O:2][C:3]([CH:5](P(OC)(OC)=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].N12CCCN=C1CCCCC2.[F:34][C:35]1[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:36]=1[CH:37]=O.C(OCC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]([NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])=[CH:37][C:36]1[C:35]([F:34])=[CH:42][CH:41]=[CH:40][C:39]=1[F:43]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
N-(Benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (Aldrich No. 37, 635-3; 6.7 g, 20 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (Aldrich No. 13, 900-9; 3.3 mL, 22 mmol) were dissolved in methylene chloride (11 mL) and stirred at room temperature for 15 min, and then cooled to <−30° C. A solution of 2,6-difluorobenzaldehyde (1.9 mL, 20 mmol) in methylene chloride (25 mL) was added to the reaction mixture dropwise over 20 min. The reaction mixture was stirred for another 20 min, and then allowed to warm up to room temperature for 30 min. The reaction mixture was then poured into ethyl ether (300 mL) and washed with 1 N HCl, brine and dried over MgSO4. Rotary evaporation gave crude 2-benzyloxycarbonylamino-3-(2,6-difluorophenyl)acrylic acid methyl ester which was purified by chromatography on a Medium Pressure Liquid Column (MPLC) eluting with 20% ethyl acetate/80% hexane to give pure product (5 g, 72% yield, liquid).
Aufarbeitung
- temperaturecooled to <−30° C
- stirringThe reaction mixture was stirred for another 20 min
- temperatureto warm up to room temperature for 30 min
- washwashed with 1 N HCl, brine
- dry with materialdried over MgSO4
- customRotary evaporation
Quellen und Nachweise
- ORD-Eintrag
- ord-89180631de3845848ba7d90fd33d5500
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07737300B2
Verknüpfte Notizen
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