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【结 构 式】 
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【分子编号】55433 【品名】tert-butyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate 【CA登记号】 |
【 分 子 式 】C15H20N2O2 【 分 子 量 】260.33608 【元素组成】C 69.2% H 7.74% N 10.76% O 12.29% |
合成路线1
该中间体在本合成路线中的序号：(I)The sulfonation of D-tryptophan tert-butyl ester (I) with 4-vinylphenylsulfonyl chloride (II) and NMM in dichloromethane gives N2-(4-vinylphenylsulfonyl)-D-tryptophan tert-butyl ester (III), which is treated with ozone in dichloromethane to yield the benzaldehyde (IV). The condensation of (IV) with phenylsulfonyl hydrazide (V) in ethanol/THF affords the phenylsulfonyl hydrazone (VI), which is cyclized with phenyldiazonium chloride (VII) (aniline, NaNO2 and aq. HCl) in pyridine to provide the tetrazole derivative (VIII). Finally, the tert-butyl ester group of (VIII) is hydrolyzed with THF in dichloromethane to furnish the target D-tryptophan derivative.
| 【1】 Watanabe, F.; Tsuzuki, H.; Ohtani, M. (Shionogi & Co. Ltd.); Sulfonated amino acid derivs. and metalloproteinase inhibitors containing the same. EP 0950656; JP 2001316254; US 6207698; US 6235768; US 6441021; WO 9727174 . |
| 【2】 Watanabe, F.; Kurihara, H.; Tamura, Y.; Sinosaki, T. (Shionogi & Co. Ltd.); Therapeutic or prophylactic agent for glomerulopathy. EP 1029541; US 6423729; WO 9904780 . |
| 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) | 55433 | tert-butyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate | C15H20N2O2 | 详情 | 详情 | |
| (II) | 55434 | 4-Vinylbenzenesulfonyl chloride; p-Styrenesulfonyl chloride; p-Vinylbenzenesulfonyl chloride; 4-Styrenesulfonyl chloride | 2633-67-2 | C8H7ClO2S | 详情 | 详情 |
| (III) | 55435 | tert-butyl (2R)-3-(1H-indol-3-yl)-2-{[(4-vinylphenyl)sulfonyl]amino}propanoate | C23H26N2O4S | 详情 | 详情 | |
| (IV) | 55436 | tert-butyl (2R)-2-{[(4-formylphenyl)sulfonyl]amino}-3-(1H-indol-3-yl)propanoate | C22H24N2O5S | 详情 | 详情 | |
| (V) | 55437 | Benzenesulfonic acid hydrazide; Benzenesulfonyl hydrazide | 80-17-1 | C6H8N2O2S | 详情 | 详情 |
| (VI) | 55438 | tert-butyl (2R)-3-(1H-indol-3-yl)-2-{[(4-{[(E)-2-(phenylsulfonyl)hydrazono]methyl}phenyl)sulfonyl]amino}propanoate | C28H30N4O6S2 | 详情 | 详情 | |
| (VII) | 25897 | benzenediazonium chloride | C6H5ClN2 | 详情 | 详情 | |
| (VIII) | 55439 | tert-butyl (2R)-3-(1H-indol-3-yl)-2-({[4-(2-phenyl-2H-1,2,3,4-tetraazol-5-yl)phenyl]sulfonyl}amino)propanoate | C28H28N6O4S | 详情 | 详情 |