- A luer Ertapenem, luer he lateral chain and its preparation method
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The invention discloses ertapenem and ertapenem side chains, as well as preparation methods of ertapenem and ertapenem side chains. L-hydroxyproline is protected by p-nitrobenzyl ester to obtain (2S,4R)-4-hydroxyl-1-(((4-Nitrobenzformyl)-oxyl)caboyl)pyrrolidine-2-carboxylic acid; then 4-nitro(1S,4S)-3-oxo-2-thia-5-azabicyclo[2.2.1]heptan-5-carboxylic anhydride can be obtained, and reacts with m-aminobenzoic acid p-nitrobenzyl ester to obtain ertapenem side chain III; and the ertapenem can be synthesized through two-step chemical reaction of condensation and deprotection to the ertapenem side chain III and a raw material MAP. An ertapenem side chain I (10), an ertapenem side chain II (13) and the ertapenem side chain III (2) which are prevailing in the market can be synthesized through simple steps, without the need of ultralow temperature, industrialization is easy, and the product purity is high, and the operation is simple and convenient.
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- Improved manufacturing method of ertapenem side chain
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The invention relates to an improved preparation method of a carbapenem compound ertapenem side chain (disclosed as Formula 1). The method comprises the following step: by using amino-protected thiolactone (disclosed as Formula I) as a raw material, carrying out reaction with 3-aminobenzoic acid under acidic conditions by using single saturated alcohol as a reaction solvent, thereby preparing the target compound. By using the single saturated alcohol as the reaction solvent, the crystal characters of the product are improved, and the production cycle is shortened. The method is economical, safe and environment-friendly, and is more suitable for the industrial production scale.
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Paragraph 0014; 0015
(2016/12/01)
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- PROCESS FOR SYNTHESIZING CARBAPENEM ANTIBIOTICS
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A process for synthesizing a coumpond of formula (I) or a pharmaceutically acceptable salt or ester thereof, wherein each P independently represents H or a protecting group, and R and R independently represent H, C1-10 alkyl, aryl or heteroaryl, or substituted C1-10 alkyl, aryl or heteroaryl, comprising: reacting the compounds (II) or a pharmaceutically acceptable salt or ester thereof, and (III) or a pharmaceutically acceptable salt or ester thereof, wherein X represents OP(O)(OR)2, or OSO2R, wherein R represents C1-6 alkyl, aryl or perfluoro C1-6 alkyl, in the presence of an amine selected from the group consisting of: diisopropylamine (DIPA), dicyclohexylamine (DCHA), 2,2,6,6-tetramethylpiperidine (TMP), 1,1,3,3-tetramethylguanidine (TMG), 1,8-diazabicyclo[4.3.0]undec-7-ene (DBU) and 1,5-diazabicyclo[4.3.0]non-5-ene to produce a compound of formula (I).
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