Diisobutylaluminum hydride → HCID 53701609、化合物

反応式

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

参加物

反応物 3

HCID 14487Diisobutylaluminum hydride

HCID 80029Trimethyl phosphonoacetate

HCID 3082435N-benzyloxycarbonylphenylalanine methyl ester

生成物 1

HCID 53701609HCID 53701609、化合物

実験手順

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.

出典と根拠

ORDレコード: ord-05bfd4e82e6a4f3381cee4991b4f908e
出典データセット: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05006511

反応ノート

読み込み中…