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【结 构 式】 
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【分子编号】52171 【品名】4-(iodomethyl)-5-methyl-1,3-dioxol-2-one 【CA登记号】 |
【 分 子 式 】C5H5IO3 【 分 子 量 】239.99737 【元素组成】C 25.02% H 2.1% I 52.88% O 20% |
合成路线1
该中间体在本合成路线中的序号：(XXI)Hydrolysis of faropenem allyl ester (XIII) to faropenem sodium (XX) can be performed under several different conditions: i) triphenylphosphine, sodium 2-ethylhexanoate and palladium tetrakis(triphenylphosphine); ii) palladium tetrakis(triphenylphosphine) and sodium 4-(methoxycarbonyl)- 5,5-dimethylcyclohexane-1,3-dione enolate in several different solvents such as methyl acetate, ethyl acetate, tetrahydrofuran, dioxane, sec-butanol, acetonitrile, acetone, 2-butanone, 1,2-dichloroethane, chlorobenzene, toluene, or ethylene glycol dimethyl ether; iii) triphenylphosphine and palladium tetrakis(triphenylphosphine) with sodium propionate, sodium acetate or sodium lactate in tetrahydrofuran or acetone; and iv) palladium acetate in the presence of P(OBu)3 and sodium propionate in THF. Finally, faropenem daloxate can be directly obtained from faropenem sodium (XX) by esterification with 4-(iodomethyl)-5-methyl-1,3-dioxol-2-one (XXI) in DMF.
| 【1】 Rabasseda, X.; Sorbera, L.A.; del Fresno, M.; Castaner, J.; Faropenem daloxate. Drugs Fut 2002, 27, 3, 223. |
| 【2】 Oyama, Y.; Imajo, S.; Tanaka, R.; Matsuki, S.; Ishiguro, M.; Structure-activity relationships of penem antibiotics: Crystallographic structures and implications for their antimicrobial activities. Bioorg Med Chem 1997, 5, 7, 1389. |
| 【3】 Jin, J.; Han, H.-N.; Liu, J.; Synthesis of the key intermediate of faropenem: (3S,4R)-3-[(R)-1-tert-Butyldimethylsilyloxyethyl]-4-[(R)-tetrahydrofuranoylthio]-2-azetidinone. J Shenyang Pharm Univ 2001, 18, 1, 20. |
| 【4】 Ishiguro, M.; Iwata, H.; Nakatsuka, T. (Suntory Ltd.); Penem cpds. AU 8654460; EP 0199446; JP 1994128267; US 4997829 . |
| 【5】 Ishiguro, M.; Yamada, Y.; Kimura, Y.; Imai, K. (Nippon Soda Co., Ltd.; Suntory Ltd.); Methods for removing allyl groups. JP 1992041489 . |
| 【6】 Iwata, H.; Nakatsuka, T.; Tanaka, R.; Ishiguro, M. (Suntory Ltd.); Antibacterial penem esters derivs.. EP 0544907; EP 0757050; JP 1994500769; JP 2000302786; US 5885981; WO 9203442 . |
| 【7】 Ishiguro, M.; Iwata, H.; Nakatsuka, T.; Nakajima, M.; Yamada, Y.; Doi, J.; Fujimaru, M. (Suntory Ltd.); Processes for removing allyl groups. EP 0410727 . |
| 【8】 Matsunaga, K.; Shimanuki, K. (Nippon Soda Co., Ltd.; Suntory Ltd.); Removal method of allyl group. JP 1994321952 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 11694 | allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C15H19NO5S | 详情 | 详情 | |
| (XX) | 52170 | sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C12H14NNaO5S | 详情 | 详情 | |
| (XXI) | 52171 | 4-(iodomethyl)-5-methyl-1,3-dioxol-2-one | C5H5IO3 | 详情 | 详情 |