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【结 构 式】 
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【分子编号】63029 【品名】tert-butyl 4-[5-[1-(tert-butoxycarbonyl)-4-piperidinyl]-3-({[2-({(2S)-3-ethoxy-2-[(2-naphthylsulfonyl)amino]-3-oxopropyl}amino)-2-oxoethyl]amino}carbonyl)pentyl]-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C43H65N5O10S 【 分 子 量 】844.0828 【元素组成】C 61.19% H 7.76% N 8.3% O 18.95% S 3.8% |
合成路线1
该中间体在本合成路线中的序号：(XIV)After activation of acid (IX) as the mixed anhydride with isobutyl chloroformate, coupling with the mono-protected diaminopropionate (X) leads to amide (XI). Subsequent removal of the N-carbobenzoxy group by catalytic hydrogenolysis gives amino ester (XII). This is then acylated by 2-naphthalenesulfonyl chloride (XIII), yielding sulfonamide (XIV).
| 【1】 Lesur, B.; Henry, M.; Yue, C.; Giboulot, T. (Laboratoires L. Lafon); Bispiperidines as antithrombotic agents. EP 1098878; FR 2781223; JP 2002520393; US 6333338; WO 0003986 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 63026 | 2-[(4-[1-(tert-butoxycarbonyl)-4-piperidinyl]-2-{2-[1-(tert-butoxycarbonyl)-4-piperidinyl]ethyl}butanoyl)amino]acetic acid | C28H49N3O7 | 详情 | 详情 | |
| (X) | 26615 | ethyl (2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propanoate | C13H18N2O4 | 详情 | 详情 | |
| (XI) | 63027 | tert-butyl 4-[(10S)-3-{2-[1-(tert-butoxycarbonyl)-4-piperidinyl]ethyl}-10-(ethoxycarbonyl)-4,7,12-trioxo-14-phenyl-13-oxa-5,8,11-triazatetradec-1-yl]-1-piperidinecarboxylate | C41H65N5O10 | 详情 | 详情 | |
| (XII) | 63028 | tert-butyl 4-{3-{[(2-{[(2S)-2-amino-3-ethoxy-3-oxopropyl]amino}-2-oxoethyl)amino]carbonyl}-5-[1-(tert-butoxycarbonyl)-4-piperidinyl]pentyl}-1-piperidinecarboxylate | C33H59N5O8 | 详情 | 详情 | |
| (XIII) | 27989 | 2-naphthalenesulfonyl chloride | 93-11-8 | C10H7ClO2S | 详情 | 详情 |
| (XIV) | 63029 | tert-butyl 4-[5-[1-(tert-butoxycarbonyl)-4-piperidinyl]-3-({[2-({(2S)-3-ethoxy-2-[(2-naphthylsulfonyl)amino]-3-oxopropyl}amino)-2-oxoethyl]amino}carbonyl)pentyl]-1-piperidinecarboxylate | C43H65N5O10S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIV)Hydrolysis of ethyl ester (XIV) employing LiOH affords the carboxylic acid (XV). The N-Boc protecting groups are finally removed by treatment with HCl in EtOAc to provide the title compound.
| 【1】 Lesur, B.; Henry, M.; Yue, C.; Giboulot, T. (Laboratoires L. Lafon); Bispiperidines as antithrombotic agents. EP 1098878; FR 2781223; JP 2002520393; US 6333338; WO 0003986 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 63029 | tert-butyl 4-[5-[1-(tert-butoxycarbonyl)-4-piperidinyl]-3-({[2-({(2S)-3-ethoxy-2-[(2-naphthylsulfonyl)amino]-3-oxopropyl}amino)-2-oxoethyl]amino}carbonyl)pentyl]-1-piperidinecarboxylate | C43H65N5O10S | 详情 | 详情 | |
| (XV) | 63031 | (2S)-3-({2-[(4-[1-(tert-butoxycarbonyl)-4-piperidinyl]-2-{2-[1-(tert-butoxycarbonyl)-4-piperidinyl]ethyl}butanoyl)amino]acetyl}amino)-2-[(2-naphthylsulfonyl)amino]propanoic acid | C41H61N5O10S | 详情 | 详情 |