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【结 构 式】 
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【分子编号】59025 【品名】methyl (3R)-3-[({(2S)-1-[(3,5-dichlorophenyl)sulfonyl]azetidinyl}carbonyl)amino]-3-(4-methoxyphenyl)propanoate 【CA登记号】 |
【 分 子 式 】C21H22Cl2N2O6S 【 分 子 量 】501.38696 【元素组成】C 50.31% H 4.42% Cl 14.14% N 5.59% O 19.15% S 6.4% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XII)Condensation of 3,5-dichlorobenzenesulfonyl chloride (VIII) with (S)-azetidine-2-carboxylic acid (IX) under Schotten-Baumann conditions gives sulfonamide (X). This is subsequently coupled with aminoester (VII) by means of PyBOP to afford amide (XI). The methyl ester group of (XI) is finally hydrolyzed to the target carboxylic acid employing LiOH.
| 【1】 Kopka, I.E.; Mumford, R.A.; Lin, L.S.; et al.; The discovery of acylated beta-amino acids as potent and orally bioavailable VLA-4 antagonists. Bioorg Med Chem Lett 2002, 12, 4, 611. |
| 【2】 Hagmann, W.K.; Durette, P.L.; Mumford, R.A.; Kopka, I.E.; Mills, S.G.; MacCoss, M.; Magriotis, P.A. (Merck & Co., Inc.); Substd. beta-alanine derivs. as cell adhesion inhibitors. WO 0071572 . |
| 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) | 59023 | 3,5-dichlorobenzenesulfonyl chloride | C6H3Cl3O2S | 详情 | 详情 | |
| (IX) | 26204 | (2S)-2-azetidinecarboxylic acid; (S)-(-)-Azetidine carboxylic acid | 2133-34-8 | C4H7NO2 | 详情 | 详情 |
| (X) | 59024 | (2S)-1-[(3,5-dichlorophenyl)sulfonyl]-2-azetidinecarboxylic acid | C10H9Cl2NO4S | 详情 | 详情 | |
| (XI) | 59022 | methyl (3R)-3-amino-3-(4-methoxyphenyl)propanoate | C11H15NO3 | 详情 | 详情 | |
| (XII) | 59025 | methyl (3R)-3-[({(2S)-1-[(3,5-dichlorophenyl)sulfonyl]azetidinyl}carbonyl)amino]-3-(4-methoxyphenyl)propanoate | C21H22Cl2N2O6S | 详情 | 详情 |
Extended Information