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【结 构 式】 
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【分子编号】51131 【品名】benzyl (2S,3R)-3-[[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-3-piperidinyl]methyl]-4-oxo-1-[[4-(6-phenylhexanoyl)-1-piperazinyl]carbonyl]-2-azetidinecarboxylate 【CA登记号】 |
【 分 子 式 】C51H58N6O9 【 分 子 量 】899.05656 【元素组成】C 68.13% H 6.5% N 9.35% O 16.02% |
合成路线1
该中间体在本合成路线中的序号：(XVII)Coupling of 6-phenylhexanoic acid (X) with N-Boc-piperazine (IX) to give (XI), followed by acid deprotection of the Boc group of (XI), provided (6-phenylhexanoyl)piperazine (XII). This was converted to the carbamoyl chloride (XIII) upon treatment with phosgene. The condensation of carbamoyl chloride (XIII) with azetidinone (VIII) gave rise to the urea derivative (XIV). After acid cleavage of the Boc protecting group of (XIV), the resulting piperidine (XV) was condensed with N,N'-dicarbobenzoxy-S-methylisothiourea (XVI) in the presence of HgCl2, yielding the protected guanidine (XVII). This was finally deprotected by catalytic hydrogenolysis over Pd/C.
| 【1】 Treuner, U.; Kronenthal, D.R.; Xu, Z.; Seiler, S.; Slusarchyk, W.A.; Bisacchi, G.; Randazzo, M.E.; Sutton, J.C.; Shi, Z.; Zahler, R.; Schwinden, M.D. (Bristol-Myers Squibb Co.); Amidino and guanidino azetidinone tryptase inhibitors. WO 9967215 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 51123 | tert-butyl 3-([(2S,3R)-2-[(benzyloxy)carbonyl]-4-oxoazetidinyl]methyl)-1-piperidinecarboxylate | C22H30N2O5 | 详情 | 详情 | |
| (IX) | 13225 | N-tert-Butoxycarbonyl piperazine; tert-butyl 1-piperazinecarboxylate;tert-butyl piperazine-1-carboxylate | 143238-38-4 | C9H18N2O2 | 详情 | 详情 |
| (X) | 51125 | 6-Phenylcaproic acid; 6-Phenylhexanoic acid; Benzenehexanoic acid | 5581-75-9 | C12H16O2 | 详情 | 详情 |
| (XI) | 51126 | tert-butyl 4-(6-phenylhexanoyl)-1-piperazinecarboxylate | C21H32N2O3 | 详情 | 详情 | |
| (XII) | 51127 | 6-phenyl-1-(1-piperazinyl)-1-hexanone | C16H24N2O | 详情 | 详情 | |
| (XIII) | 51128 | 4-(6-phenylhexanoyl)-1-piperazinecarbonyl chloride | C17H23ClN2O2 | 详情 | 详情 | |
| (XIV) | 51129 | tert-butyl 3-[((2S,3R)-2-[(benzyloxy)carbonyl]-4-oxo-1-[[4-(6-phenylhexanoyl)-1-piperazinyl]carbonyl]azetidinyl)methyl]-1-piperidinecarboxylate | C39H52N4O7 | 详情 | 详情 | |
| (XV) | 51130 | benzyl (2S,3R)-4-oxo-1-[[4-(6-phenylhexanoyl)-1-piperazinyl]carbonyl]-3-(3-piperidinylmethyl)-2-azetidinecarboxylate | C34H44N4O5 | 详情 | 详情 | |
| (XVI) | 32861 | benzyl (E)-[[(benzyloxy)carbonyl]amino](methylsulfanyl)methylidenecarbamate | C18H18N2O4S | 详情 | 详情 | |
| (XVII) | 51131 | benzyl (2S,3R)-3-[[1-([[(benzyloxy)carbonyl]amino][[(benzyloxy)carbonyl]imino]methyl)-3-piperidinyl]methyl]-4-oxo-1-[[4-(6-phenylhexanoyl)-1-piperazinyl]carbonyl]-2-azetidinecarboxylate | C51H58N6O9 | 详情 | 详情 |