Reaktionsgleichung
[CH2:1]([C:3]1[C:4](=O)[N:5]([C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17](S(NC(NC3CCC(C)CC3)=O)(=O)=O)=[CH:16][CH:15]=2)=[O:10])[CH2:6][C:7]=1[CH3:8])[CH3:2].CCC1[C:41](=[O:42])N(C(NCCC2C=CC(S(NC(N[C@@H]3CC[C@@H](C)CC3)=O)(=O)=O)=CC=2)=O)CC=1C.C1(CCN=C=O)C=CC=CC=1>>[CH2:1]([CH:3]1[CH:7]([CH3:8])[CH2:6][N:5]([C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])[C:4]1=[C:41]=[O:42])[CH3:2]Komponenten
Versuchsvorschrift
U.S. Pat. No. 4,379,785 (hereinafter referred to as the '785 patent) discloses heterocyclic substituted sulfonylureas, particularly N-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-N′-4-methylcyclohexylurea i.e. glimepiride. The '785 patent teaches the preparation of glimepiride starting from 3-Ethyl-4-methyl-3-pyrrolidin-2-one and 2-phenylethylisocyanate to give [2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene. The [2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene is converted to the 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene sulfonamide, a compound of formula 4, by reacting with chlorosulfonic acid, followed by treatment with ammonia solution. This intermediate compound of formula 4 is further reacted with trans-4-methylyclohexyl isocyanate to form glimepiride. The '785 patent teaches a three step process for preparation of the intermediate compound of formula 4, i.e. 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido)ethyl]benzene sulfonamide, which is represented in Scheme 1.
Quellen und Nachweise
- ORD-Eintrag
- ord-095a48c0bf0d4c9aa0cc112215eb4dd4
- Quelldatensatz
- uspto-grants-2006_11
- Patentnummer
- US07132444B2
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