Diisobutylaluminum hydride → HCID 53701609, compound

HRID 1084688Notes

Reaction equation

HRID 1084688 reaction equation
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

Participants

4

Reactant 3

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

Product 1

HCID 53701609HCID 53701609, compound

Procedure

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.

Sources & evidence

ORD record
ord-05bfd4e82e6a4f3381cee4991b4f908e
Source dataset
uspto-grants-1991_04
Patent number
US05006511

Reaction notes

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