Reaktionsgleichung
[C@H:1]12[CH2:6][C@H:5]1[CH2:4][C@@H:3]([C:7]#[N:8])[NH:2]2.[CH2:9]([O:16][C:17]([NH:19][C@@H:20]([C:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][C:26]([OH:34])([CH2:27]3)[CH2:25]1)[CH2:31]2)[C:21](O)=[O:22])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:7]([C@@H:3]1[CH2:4][C@H:5]2[C@H:1]([CH2:6]2)[N:2]1[C:21](=[O:22])[C@@H:20]([NH:19][C:17](=[O:18])[O:16][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][C:26]([OH:34])([CH2:27]3)[CH2:25]1)[CH2:31]2)#[N:8]Komponenten
Versuchsvorschrift
Path A: (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carbonitrile or its salts of formula-XIII can be coupled with (2S)-2-{[(benzyloxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acid of formula-XIV to give benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo-ethyl]carbamate of Formula-XI in a suitable solvent, for example, tetrahydrofuran, N,N-dimethyl formamide, 1,4-dioxane or ethyl acetate using a coupling agent, for example, 1,3-dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3′-dimethyl amino propyl)carbodiimide (EDAC), 1-propane phosphonic acid cyclic anhydride or N-[(dimethylamino)-1H-1,2,3-trizole[4,5-b]pyridylmethylene]-N-methylmethanaminium hexafluoro phosphate N-oxide (HATU) and optionally, a catalyst, for example, 1-hydroxybenzotriazole (HOBT) or 7-aza-hydroxylbenzotriazole (HOAt) and optionally, with a base, for example, N,N-dimethylamino pyridine (DMAP), triethylamine, N,N-diisopropylethylamine or N-methyl morpholine.
Quellen und Nachweise
- ORD-Eintrag
- ord-822f976a9c6e4fa886efd356f7dbd463
- Quelldatensatz
- uspto-grants-2014_03
- Patentnummer
- US08664443B2
Verknüpfte Notizen
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