Diisobutylaluminum hydride → HCID 53701609, Verbindung

HRID 1084688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1084688
CO[C:3](=O)[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].CC(C[AlH]CC(C)C)C.[CH3:33][O:34][C:35]([CH2:37]P(OC)(OC)=O)=[O:36]>>[CH2:9]([O:8][C:6]([NH:5][CH:4]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:3]=[CH:37][C:35]([O:34][CH3:33])=[O:36])=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 3

HCID 14487Diisobutylaluminum hydrideHCID 80029Trimethyl phosphonoacetateHCID 3082435N-benzyloxycarbonylphenylalanine methyl ester

Produkt 1

HCID 53701609HCID 53701609, Verbindung

Versuchsvorschrift

N-Benzyloxycarbonyl phenylalanine methyl ester is reduced with DIBAL to the aldehyde using the procedure of Boger et al., J. Med. Chem. (1985) 28, 1779, which is homologated with the sodio derivative of trimethyl phosphonoacetate using the procedure of Wadsworth and Emmons, Org. Synth. (1965) 45, 44 to give methyl 4-(benzyloxycarbonyl)amino-5-phenyl-2-pentenoate.

Quellen und Nachweise

ORD-Eintrag
ord-05bfd4e82e6a4f3381cee4991b4f908e
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006511

Notizen zur Reaktion

Wird geladen…