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【结 构 式】 
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【分子编号】62822 【品名】methyl (2S)-3-[1,1'-biphenyl]-4-yl-2-[({1-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]propanoate 【CA登记号】 |
【 分 子 式 】C27H34N2O5 【 分 子 量 】466.57744 【元素组成】C 69.51% H 7.34% N 6% O 17.15% |
合成路线1
该中间体在本合成路线中的序号：(VII)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).
| 【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 |