158299-05-9Relevant articles and documents
Preparation method of 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one as meropenem intermediate
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Paragraph 0070-0072, (2017/05/12)
The invention provides a preparation method of 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one as a meropenem intermediate. According to the preparation method, alpha-chloropropionyl chloride with lower reaction activity is adopted and cooperates with specific raw materials to play a role together, so that the reaction yield is greatly increased instead of being reduced; meanwhile, due to the lower activity of alpha-chloropropionyl chloride, fewer side reactions participate in the reaction, an obtained product contains fewer impurities, and 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one with higher yield and purity is obtained and can replace 3-(2-bromo-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one for preparing meropenem. Besides, a synthetic process of 3-(2-chloro-1-oxopropyl)-spiro[2H-1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one requires no magnetic solid base catalysts, so that the reaction conditions are safer, the reaction path is simple, aftertreatment is convenient, the raw materials and the catalyst are inexpensive and available, and the preparation method is safe, environment-friendly, lower in preparation cost and more suitable for industrial production.
2-Substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones: Novel auxiliaries for stereoselective synthesis of 1-β-methylcarbapenems
Kondo,Seki,Kuroda,Yamanaka,Iwasaki
, p. 2877 - 2884 (2007/10/03)
The dihydrobenzoxazone 9e, which is easily prepared from salicylamide 11 and cyclohexanone, serves as an efficient auxiliary in the synthesis of the 1-β-methylcarbapenem key intermediate 10. The stereocontrolled Reformatsky-type reactions of the acetoxyazetidinone 2 with the carboximides 6 gave the intermediates 7 with high diastereoselectivities in high chemical yields. The auxiliary 9e also acts as a good leaving guoup in the TMSCl-promoted Dieckmann-type cyclization leading to a 1-β-methylcarbapenem skeleton. By using this auxiliary, 10 was synthesized in 58% overall yield and four steps from 2.
2-Substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones: A novel auxiliary for stereoselective synthesis of 1-β-methylcarbapenems
Kondo,Seki,Kuroda,Yamanaka,Iwasaki
, p. 1096 - 1097 (2007/10/02)
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