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【结 构 式】

【药物名称】

【化学名称】4(S)-(Benzyloxycarbonyl-L-leucyl-L-phenylalanylamino)-6-carbamoyl-2(E)-hexenoic acid ethyl ester

【CA登记号】

【 分 子 式 】C32H42N4O7

【 分 子 量 】594.71414

【开发单位】Agouron (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Anti-Rhinovirus Drugs, Antiviral Drugs, Protease Inhibitors

合成路线1

The condensation of the protected L-glutamine (I) with N,O-dimethylhydroxylamine (II) by means of isobutyl chloroformate and NMM in dichloromethane gives the methoxyamide (III), which is reduced with DIBAL in THF to the aldehyde (IV). The condensation of (IV) with phosphonate (V) by means of NaN(SiMe3)2 in THF yields the carbamoylhexenoate (VI), which is selectively deprotected with HCl in dioxane and condensed with the dipeptide (VII) by means of HOBT, NMM and EDC in dichloromethane to afford the tritylated target compound (VIII). Finally, the trityl group of (VIII) is eliminated with TFA and Et3SiH in dichloromethane.

1 Dragovich, P.S.; Babine, R.E.; Webber, S.E.; et al.; Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 1. Michael acceptor structure-activity studies. J Med Chem 1998, 41, 15, 2806.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 31045 (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxo-5-(tritylamino)pentanoic acid C29H32N2O5 详情 详情
(II) 13361 (Methoxyamino)methane; N,O-Dimethylhydroxylamine 1117-97-1 C2H7NO 详情 详情
(III) 31046 tert-butyl (1S)-1-[[methoxy(methyl)amino]carbonyl]-4-oxo-4-(tritylamino)butylcarbamate C31H37N3O5 详情 详情
(IV) 31047 tert-butyl (1S)-1-formyl-4-oxo-4-(tritylamino)butylcarbamate C29H32N2O4 详情 详情
(V) 10019 Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate 867-13-0 C8H17O5P 详情 详情
(VI) 31048 ethyl (E,4S)-4-[(tert-butoxycarbonyl)amino]-7-oxo-7-(tritylamino)-2-heptenoate C33H38N2O5 详情 详情
(VII) 31052 (2S)-2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoyl)amino]-3-phenylpropionic acid C23H28N2O5 详情 详情
(VII) 31053 ethyl (5S,8S,11S,12E)-11-(3-amino-3-oxopropyl)-8-benzyl-5-isobutyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triaza-12-tetradecen-14-oate C32H42N4O7 详情 详情
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