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【结 构 式】 
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【分子编号】19595 【品名】methyl (E)-3-[6-[[(4-chlorophenyl)sulfonyl]amino]-3-(3-pyridinylmethyl)-5,6,7,8-tetrahydro-1-naphthalenyl]-2-propenoate 【CA登记号】 |
【 分 子 式 】C26H25ClN2O4S 【 分 子 量 】497.01428 【元素组成】C 62.83% H 5.07% Cl 7.13% N 5.64% O 12.88% S 6.45% |
合成路线1
该中间体在本合成路线中的序号：(XX)The alcohol (XV) was oxidized with 4-benzylpyridinium dichromate to the aldehyde (XVI). 3-(Tributylstannylmethyl)pyridine (XVIII), prepared from lithiated 3-picoline (XVII) and Bu3SnCl in the presence of HMPA, was coupled to bromotetrahydronaphthalene (XVI) under palladium catalysis to provide the pyridylmethyl derivative (XIX). Wittig reaction of (XIX) with phosphorane (IX) gave acrylate (XX), which was reduced with NaBH4 and CoCl2 to the tetrahydronaphthylpropionic ester (XXI). Finally, the ester group of (XXI) was hydrolyzed with NaOH in MeOH-H2O to give the title acid.
| 【1】 Cimetière, B.; Dubuffet, T.; Landras, C.; Descombes, J.J.; Simonet, S.; Verbeuren, T.J.; Lavielle, G.; New tetrahydronaphthalene derivatives as combined thromboxane receptor antagonists and thromboxane synthase inhibitors. Bioorg Med Chem Lett 1998, 8, 11, 1381. |
| 【2】 Lavielle, G.; Dubuffet, T.; Muller, O.; Laubie, M.; Verbeuren, T.; Simonet, S.; Descombes, J.-J. (ADIR et Cie.); 1,2,3,4-Tetrahydronaphthalene, chroman and thiochroman derivs. as antithrombotic agents. CA 2118102; EP 0648741; FR 2711139; JP 1995188155 . |
| 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) | 14689 | Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate | 2605-67-6 | C21H19O2P | 详情 | 详情 |
| (XVI) | 19591 | N-(7-bromo-5-formyl-1,2,3,4-tetrahydro-2-naphthalenyl)-4-chlorobenzenesulfonamide | C17H15BrClNO3S | 详情 | 详情 | |
| (XVII) | 19592 | (3-pyridinylmethyl)lithium | C6H6LiN | 详情 | 详情 | |
| (XVIII) | 19572 | 3-[(tributylstannyl)methyl]pyridine | C18H33NSn | 详情 | 详情 | |
| (XIX) | 19594 | 4-chloro-N-[5-formyl-7-(3-pyridinylmethyl)-1,2,3,4-tetrahydro-2-naphthalenyl]benzenesulfonamide | C23H21ClN2O3S | 详情 | 详情 | |
| (XX) | 19595 | methyl (E)-3-[6-[[(4-chlorophenyl)sulfonyl]amino]-3-(3-pyridinylmethyl)-5,6,7,8-tetrahydro-1-naphthalenyl]-2-propenoate | C26H25ClN2O4S | 详情 | 详情 | |
| (XXI) | 19596 | methyl 3-[6-[[(4-chlorophenyl)sulfonyl]amino]-3-(3-pyridinylmethyl)-5,6,7,8-tetrahydro-1-naphthalenyl]propanoate | C26H27ClN2O4S | 详情 | 详情 |