Reaktionsgleichung
[F:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]([OH:15])=O)[S:10][C:6]=2[C:5]([F:16])=[CH:4][C:3]=1[F:17].S(Cl)(Cl)=O.Cl.[CH3:23][O:24][C:25](=[O:34])[CH2:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.O>[CH3:23][O:24][C:25](=[O:34])[CH2:26][N:27]([C:13](=[O:15])[CH2:12][CH2:11][C:9]1[S:10][C:6]2[C:5]([F:16])=[CH:4][C:3]([F:17])=[C:2]([F:1])[C:7]=2[N:8]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
To a solution of 3-(4,5,7-trifluorobenzothiazol-2-yl)propionic acid (522 mg, 2 mmol) obtained in Example 3-i) in a mixture of toluene (5 ml) and N,N-dimethylformamide (DMF; 1 ml) was added thionyl chloride (357 mg, 3 mmol) and the mixture was stirred for 1 hour at room temperature. To the ice cold reaction mixture was N-phenylglycine methyl ester hydrochloride (403 mg, 2 mmol) and triethylamine (400 mg, 4 mmol) and the mixture was stirred for 2 hours. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water, then dried and evaporated to yield a residue, which was purified on a silica gel column to give N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycine methyl ester (240 mg, 29%) as an oil.
Aufarbeitung
- stirringthe mixture was stirred for 2 hours
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- customdried
- customevaporated
- customto yield a residue, which
- customwas purified on a silica gel column
Quellen und Nachweise
- ORD-Eintrag
- ord-37a26dca2893411c94de2c3f45e583a0
- Quelldatensatz
- uspto-grants-1997_12
- Patentnummer
- US05700819
Verknüpfte Notizen
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