Alaptide, VUFB-15754, CPA, c(Acp-Ala), -Drug Synthesis Database

【结构式】

【药物名称】Alaptide, VUFB-15754, CPA, c(Acp-Ala)

【化学名称】Cyclo(1-amino-1-cyclopentanecarbonyl-L-alanyl)
　　　　　　6'(S)-Methyl-2',5'-dioxospiro[cyclopentane-1,3'-piperazine]
　　　　　　8(S)-Methyl-6,9-diazaspiro[4.5]decane-7,10-dione

【CA登记号】90058-29-0

【分子式】C₉H₁₄N₂O₂

【分子量】182.22413

【开发单位】Res. Inst. Pharmacy Biochemistry (VUFB) (Originator)

【药理作用】Antiulcer Drugs, DERMATOLOGIC DRUGS, GASTROINTESTINAL DRUGS, Ulcers of the Extremities, Agents for

合成路线1

The condensation of methyl 1-aminocyclopentane-1-carboxylate (I) with N-benzyloxycarbonyl-alanine (II) by the mixed anhydride method gives methyl 1-(benzyloxycarbonyl-alanyl)aminocyclopentane-1-carboxylate (III). Debenzylation of (III) by hydrogenation with H2 over Pd/C in methanol followed by a cyclization reaction in refluxing toluene yields alaptide.

参考文献中间体

【1】 Kasafirek, E.; Vanzura, J.; Krejci, I.; Krepelka, J.; Dlabac, A.; Valchar, M. (SPOFA - United Pharmaceutical Works); 2,5-Piperazinedione derivs. CS 231227; GB 2127807 .
【2】 Rádl, S.; Kasafírek, E.; Krejcí, I.; ALAPTIDE. Drugs Fut 1990, 15, 5, 445.

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)	10444	methyl 1-aminocyclopentanecarboxylate		C₇H₁₃NO₂	详情	详情
(II)	10445	N-Carbobenzyloxy-L-alanine;N-Benzyloxycarbonyl-L-alanine;Carbobenzyloxy-L-alanine;Z-L-Alanine;Z-Ala-OH;BenzyloxycarbonylLalanine;N-Cbz-L-alanine	1142-20-7	C₁₁H₁₃NO₄	详情	详情
(III)	10446	methyl 1-[((2S)-2-[[(benzyloxy)carbonyl]amino]propanoyl)amino]cyclopentanecarboxylate		C₁₈H₂₄N₂O₅	详情	详情

Extended Information