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【结 构 式】 
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【分子编号】27335 【品名】Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine 【CA登记号】4795-29-3 |
【 分 子 式 】C5H11NO 【 分 子 量 】101.14848 【元素组成】C 59.37% H 10.96% N 13.85% O 15.82% |
合成路线1
该中间体在本合成路线中的序号：(IV)2-Methoxy-5-(N-methylmethanesulfonamido)-N-tetrahydrofurfurylbenzamide (II), which is prepared from (I) and tetrahydrofurfurylamine, is treated with SOCl2 in dichloroethane to give the dichloro compound (III). Treatment of (III) with EtNH2 gives title compound.
| 【1】 Masaru, O.; Hiroshi, M. (Shionogi & Co. Ltd.); Meta-sulfonamido-benzamides. DE 2803651; ES 466366; FR 2378758; GB 1557019; US 4328155; US 4328344; US 4330472; US 4350635; US 4351770; US 44313663 . |
| 【2】 Ogata, M.; 710723-S. Drugs Fut 1985, 10, 9, 758. |
| 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) | 27331 | 2-methoxy-5-[methyl(methylsulfonyl)amino]benzoic acid | C10H13NO5S | 详情 | 详情 | |
| (II) | 27333 | 2-methoxy-5-[methyl(methylsulfonyl)amino]-N-(tetrahydro-3-furanylmethyl)benzamide | C15H22N2O5S | 详情 | 详情 | |
| (III) | 27334 | N-(2,5-dichloropentyl)-2-methoxy-5-[methyl(methylsulfonyl)amino]benzamide | C15H22Cl2N2O4S | 详情 | 详情 | |
| (IV) | 27335 | Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine | 4795-29-3 | C5H11NO | 详情 | 详情 |
| (V) | 10928 | Ethanamine | 75-04-7 | C2H7N | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(LXVII)Tetrahydrofurfurylamine (XLVII) was converted into the corresponding phthalimide (XLVIII) by reaction of phthalic anhydride (V) in boiling chloroform. Subsequent ruthenium-catalyzed oxidation of (XLVIII) produced keto acid (XI), along with a pentanolide by-product, which was removed by column chromatography. Finally, acid hydrolysis of (XI) led to the desired compound. A closely related strategy was based in the ruthenium oxidation of N-benzoyl tetrahydrofurfurylamine (LXX), prepared from amine (XLVII) and benzoyl chloride (XLIX), to afford 5-benzoylaminolevulinic acid (XXXV), which was then hydrolyzed in boiling 6 N HCl .
| 【1】 Kawakami, H.; et al.; A new synthesis of 5-aminolevulinic acid. Agric Biol Chem 1991, 55, 6, 1687. |
| 【2】 Matsumoto, K.; Kawakami, H.; Koseki, K.; Ebata, T.; Matsushita, H. (Japan Tobacco Inc.); Method of preparing an acid additional salt of delta-aminolevulinic acid. US 5284973 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |
| (XI) | 59147 | 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoic acid | C13H11NO5 | 详情 | 详情 | |
| (XXXV) | 59156 | 5-(benzoylamino)-4-oxopentanoic acid | C12H13NO4 | 详情 | 详情 | |
| (LXVII) | 27335 | Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine | 4795-29-3 | C5H11NO | 详情 | 详情 |
| (LXVIII) | 59191 | 2-(tetrahydro-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione | C13H13NO3 | 详情 | 详情 | |
| (LXIX) | 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 |
| (LXX) | 59192 | N-(tetrahydro-2-furanylmethyl)benzamide | C12H15NO2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(VI)The reaction of m-xylene-alpha,alpha'-diamine (I) with N,N'-bis(tert-butoxycarbonyl)pyrazole-1-carboxamidine (II) in THF gives the protected guanidine (III), which is acylated at the free amino group with 2,3-diphenylpropionyl chloride (IV) and triethylamine in dichloromethane affording the amide (V). The condensation of (V) with tetrahydrofuran-2-ylmethylamine (VI) in refluxing THF affords the protected amidinourea (VII), which is finally treated with TFA in dichloromethane.
| 【1】 Biftu, T.; et al.; Synthesis and SAR of oxodiazole benzenesulfonamides as selective beta3 adrenergic receptor agonist antiobesity agents. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 138. |
| 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) | 19167 | 3-(aminomethyl)benzylamine; [3-(aminomethyl)phenyl]methanamine | 1477-55-0 | C8H12N2 | 详情 | 详情 |
| (II) | 29482 | N,N-bis-Boc-1-guanylpyrazole; tert-butyl (E)-[(tert-butoxycarbonyl)amino](1H-pyrazol-1-yl)methylidenecarbamate | 152120-54-2 | C14H22N4O4 | 详情 | 详情 |
| (III) | 29483 | tert-butyl (Z)-[[3-(aminomethyl)benzyl]amino][(tert-butoxycarbonyl)amino]methylidenecarbamate | C19H30N4O4 | 详情 | 详情 | |
| (IV) | 29484 | 2,3-diphenylpropanoyl chloride | C15H13ClO | 详情 | 详情 | |
| (V) | 29485 | tert-butyl (Z)-[(tert-butoxycarbonyl)amino][(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]methylidenecarbamate | C34H42N4O5 | 详情 | 详情 | |
| (VI) | 27335 | Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine | 4795-29-3 | C5H11NO | 详情 | 详情 |
| (VII) | 29486 | tert-butyl (Z)-[(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]([[(tetrahydro-2-furanylmethyl)amino]carbonyl]amino)methylidenecarbamate | C35H43N5O5 | 详情 | 详情 |