Reaktionsgleichung
COC(OC)C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][O:46][CH:47]([O:50][CH3:51])[CH2:48]Br.[CH3:52][CH:53]([CH3:60])[CH2:54][C:55](=O)[C:56]([OH:58])=[O:57]>>[CH3:45][O:46][CH:47]([O:50][CH3:51])[CH2:48][CH:55]([CH2:54][CH:53]([CH3:60])[CH3:52])[C:56]([OH:58])=[O:57]Komponenten
Versuchsvorschrift
Alternatively, for those compounds wherein n=1 and R1 is H, the compounds can be prepared by condensing the ylide 1,1-dimethoxy-2-(triphenylphosphoranylidene) ethane prepared from triphenylphosphine and 1,1-dimethoxy-2-bromoethane with 4-methyl-2-oxopentanoic acid. The product is then hydrogenated to obtain 4,4-dimethoxy-2-isobutylbutanoic acid which is coupled to the moiety R3NHCHR4COX to obtain 4,4-dimethoxy-2-isobutylbutanoyl--NR3CHR4COX. Treatment with aqueous acid yields the aldehyde 2-isobutyl-4-oxobutanoyl--NR3CHR4COX. The oxime is prepared by reaction with hydroxylamine and reduced to the corresponding N-substituted hydroxylamine. Acylation of both the hydroxaminol oxygen and nitrogen followed by hydrolysis of the O-acyl group provides the N-acyl reverse hydroxymates. (Summers, J.B., et al., J Med Chem (1988) 31:1960-1964.)
Quellen und Nachweise
- ORD-Eintrag
- ord-d12e82eadbdf4628b606f1573211d8b5
- Quelldatensatz
- uspto-grants-1993_12
- Patentnummer
- US05268384
Verknüpfte Notizen
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