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【结 构 式】 
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【分子编号】50891 【品名】ethyl (2S)-2-[(4-[4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl)amino]-1-piperidinyl]benzoyl)amino]-4-methylpentanoate 【CA登记号】 |
【 分 子 式 】C29H42N4O7S 【 分 子 量 】590.74124 【元素组成】C 58.96% H 7.17% N 9.48% O 18.96% S 5.43% |
合成路线1
该中间体在本合成路线中的序号：(IX)Condensation of ethyl 4-fluorobenzoate (I) with 4-piperidone ethylene ketal (II) afforded the N-arylpiperidine (III). Saponification of the ethyl ester group of (III), followed by acidic hydrolysis of the ethylene ketal function, yielded the benzoic acid derivative (V). Coupling of acid (V) with leucine ethyl ester (VI) using EDC gave amide (VII). Then, reductive amination of piperidone (VII) with the known arylethanolamine (VIII) using NaBH(OAc)3 furnished the aminopiperidine (IX). The ethyl ester group of (IX) was finally hydrolyzed with NaOH to provide the corresponding carboxylic acid.
| 【1】 Hu, B.; et al.; (4-Piperidin-1-yl)phenyl amides: Potent and selective human beta3 agonists. J Med Chem 2001, 44, 9, 1456. |
| 【2】 Taylor, E.C.; Skotnicki, J.S.; A convenient synthesis of 1-aryl-4-piperidones. Synthesis 1981, 606. |
| 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) | 22830 | ethyl 4-fluorobenzoate | 451-46-7 | C9H9FO2 | 详情 | 详情 |
| (II) | 11338 | 1,4-Dioxa-8-azaspiro[4.5]decane; 4-Piperidone ethylene ketal | 177-11-7 | C7H13NO2 | 详情 | 详情 |
| (III) | 50886 | ethyl 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoate | C16H21NO4 | 详情 | 详情 | |
| (IV) | 50887 | 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoic acid | C14H17NO4 | 详情 | 详情 | |
| (V) | 50888 | 4-(4-oxo-1-piperidinyl)benzoic acid | C12H13NO3 | 详情 | 详情 | |
| (VI) | 50889 | ethyl (2S)-2-amino-4-methylpentanoate | C8H17NO2 | 详情 | 详情 | |
| (VII) | 50890 | ethyl (2S)-4-methyl-2-[[4-(4-oxo-1-piperidinyl)benzoyl]amino]pentanoate | C20H28N2O4 | 详情 | 详情 | |
| (VIII) | 49404 | N-[5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide | C9H14N2O4S | 详情 | 详情 | |
| (IX) | 50891 | ethyl (2S)-2-[(4-[4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl)amino]-1-piperidinyl]benzoyl)amino]-4-methylpentanoate | C29H42N4O7S | 详情 | 详情 |