Reaktionsgleichung
[CH:1]1([C:5]2[N:6]=[C:7](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:30])[CH2:20][C:21]4[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=4[C:23]([OH:25])=[O:24])[CH:15]=[CH:16][CH:17]=3)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:31](OCC)C.[N+](=C)=[N-]>C(OCC)C.C(Cl)Cl>[CH3:31][O:24][C:23](=[O:25])[C:22]1[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=1[CH2:20][C:19]([NH:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12](/[CH:11]=[CH:10]/[C:7]2[S:8][CH:9]=[C:5]([CH:1]3[CH2:2][CH2:3][CH2:4]3)[N:6]=2)[CH:13]=1)=[O:30]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A suspension of 2.1 g of (E)-2-[2-[3-[2-[4-(cyclobuty)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid in 200 ml of ethyl ether/methylene chloride (1:3 v/v) was treated with an excess of an ethyl ether solution of diazomethane. After 10 min the excess of diazomethane was removed with a stream of nitrogen, the remaining solvents were removed in vacuo and the residual materials were taken up into methylene chloride. This solution was washed with water (2×15 ml) and dried (MgSO4). Removal of the volatiles in vacuo and recrystallization from ethyl acetate yielded 2.2 g of (E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid methyl ester as an off-white solid, m.p. 143°-144° C. Anal. Calcd for C25H24N2O3S: C, 69.42; H, 5.59; N, 6.48. Found: C, 69.21; H, 5.63; N, 6.49.
Aufarbeitung
- customAfter 10 min the excess of diazomethane was removed with a stream of nitrogen
- customthe remaining solvents were removed in vacuo
- washThis solution was washed with water (2×15 ml)
- dry with materialdried (MgSO4)
- customRemoval of the volatiles
- customin vacuo and recrystallization from ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-f3a7aa00d2104afc90908f85a317610b
- Quelldatensatz
- uspto-grants-1993_12
- Patentnummer
- US05273986
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