MX-1013, Z-VD-fmk, CV-1013, -Drug Synthesis Database

【结构式】

【药物名称】MX-1013, Z-VD-fmk, CV-1013

【化学名称】N-(Benzyloxycarbonyl)-L-valyl-DL-aspartyl-fluoromethane

【CA登记号】223568-55-6 ((S)-isomer)

【分子式】C₁₈H₂₃FN₂O₆

【分子量】382.39221

【开发单位】Cytovia (Originator), Maxim (Licensee)

【药理作用】Acute Myocardial Infarction, Treatment of, CARDIOVASCULAR DRUGS, Cerebrovascular Diseases, Treatment of, GASTROINTESTINAL DRUGS, Liver and Biliary Tract Disorders, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Apoptosis Inhibitors, Caspase Inhibitors

合成路线1

2-Fluoroethanol (I) was oxidized under Swern conditions to afford 2-fluoroacetaldehyde (II), which was condensed with tert-butyl 3-nitropropionate (III), yielding the hydroxy ester (IV). Hydrogenation of the nitro group of (IV) over Raney nickel produced amine (V). Subsequent coupling of N-carbobenzoxy-L-valine (VI) with amine (V) in the presence of EDC and HOBt furnished amide (VII). The hydroxyl group of (VII) was then oxidized to the corresponding ketone (VIII) by using Dess-Martin periodinane. Finally, the tert-butyl ester was cleaved by treatment with trifluoroacetic acid.

参考文献中间体

【1】 Guastella, J.; Yang, W.; Cai, S.X.; Keana, J.F.W.; Drewe, J.A. (Cytovia, Inc.); Dipeptide apoptosis inhibitors and the use thereof. EP 1033910; US 6184210; WO 9918781 .

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)	44106	2-fluoro-1-ethanol	371-62-0	C₂H₅FO	详情	详情
(II)	44107	2-fluoroacetaldehyde		C₂H₃FO	详情	详情
(III)	44108	tert-butyl 3-nitropropanoate		C₇H₁₃NO₄	详情	详情
(IV)	44109	tert-butyl 5-fluoro-4-hydroxy-3-nitropentanoate		C₉H₁₆FNO₅	详情	详情
(V)	44110	tert-butyl 3-amino-5-fluoro-4-hydroxypentanoate		C₉H₁₈FNO₃	详情	详情
(VI)	18092	(2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid		C₁₃H₁₇NO₄	详情	详情
(VII)	44111	tert-butyl 3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-5-fluoro-4-hydroxypentanoate		C₂₂H₃₃FN₂O₆	详情	详情
(VIII)	44112	tert-butyl 3-[((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)amino]-5-fluoro-4-oxopentanoate		C₂₂H₃₁FN₂O₆	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)