methyl 1-aminocyclopentanecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】10444

【品名】methyl 1-aminocyclopentanecarboxylate

【CA登记号】

【分子式】C₇H₁₃NO₂

【分子量】143.18576

【元素组成】C 58.72% H 9.15% N 9.78% O 22.35%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

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

合成目标

【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

合成路线2

该中间体在本合成路线中的序号：(II)

Cycloleucine (I) is esterified with HCl/MeOH, and the resultant amino ester (II) is further protected as the tert-butyl carbamate (III) employing Boc2O and Et3N in CH2Cl2. Then, hydrolysis of the methyl ester group of (III) with LiOH furnishes N-Boc-cycloleucine (IV). N-Boc-L-Biphenylalanine (V) is simultaneously deprotected and esterified with HCl/MeOH to yield amino ester (VI). Coupling between N-Boc-cycloleucine (IV) and L-biphenylalanine methyl ester (VI) in the presence of EDC/HOAt gives rise to the protected dipeptide (VII). Subsequent removal of the N-Boc group of (VII) under acidic conditions yields the dipeptide methyl ester (VIII).

参考文献中间体

合成目标

【1】 Fink, C.A.; De Lombaert, S.; Hoyer, D.W.; Jeng, A.Y.; Firoozina, F. (Novartis AG; Novartis Pharma GmbH); Certain thiol inhibitors of endothelin-converting enzyme. WO 9955726 .

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)	33149	1-aminocyclopentanecarboxylic acid	52-52-8	C₆H₁₁NO₂	详情	详情
(II)	10444	methyl 1-aminocyclopentanecarboxylate		C₇H₁₃NO₂	详情	详情
(III)	62819	methyl 1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate		C₁₂H₂₁NO₄	详情	详情
(IV)	30890	1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid		C₁₁H₁₉NO₄	详情	详情
(V)	62820	(2S)-3-[1,1'-biphenyl]-4-yl-2-[(tert-butoxycarbonyl)amino]propanoic acid		C₂₀H₂₃NO₄	详情	详情
(VI)	62821	methyl (2S)-2-amino-3-[1,1'-biphenyl]-4-ylpropanoate		C₁₆H₁₇NO₂	详情	详情
(VII)	62822	methyl (2S)-3-[1,1'-biphenyl]-4-yl-2-[({1-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]propanoate		C₂₇H₃₄N₂O₅	详情	详情
(VIII)	62823	methyl (2S)-2-{[(1-aminocyclopentyl)carbonyl]amino}-3-[1,1'-biphenyl]-4-ylpropanoate		C₂₂H₂₆N₂O₃	详情	详情

Extended Information