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Process for production of intermediate for meropenem

A solid, compound technology, applied in the field of preparation of meropenem intermediates, can solve problems such as unsatisfactory implementation on an industrial scale

Inactive Publication Date: 2009-04-15
KANEKA CORP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Patent Document 2 discloses a method for isolating compound (1). However, in the method of crystallization and separation from an alkyl alkanoic acid solvent alone, even if a poor solvent is added during the separation operation, stirring is required at 20°C for a long time. 72+ hours, unsatisfactory implementation on an industrial scale

Method used

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  • Process for production of intermediate for meropenem
  • Process for production of intermediate for meropenem
  • Process for production of intermediate for meropenem

Examples

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reference example 1

[0097] Preparation of (4R,5S,6S)-3-[[(3S,5S)-1-(p-Nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]thio]- 6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate p-nitrobenzyl ester (1 ) in a good solvent solution

[0098] [chemical 5]

[0099]

[0100] 40.0g (4R, 5S, 6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo [3.2.0] p-nitrobenzyl hept-2-ene-2-carboxylate and 25.0g (2S, 4S)-2-dimethylaminocarbonyl-4-mercapto-1-(p-nitrobenzyloxycarbonyl )-pyrrolidine was added to 120ml of acetonitrile, and cooled to -10°C while stirring. 10.5 g of N,N-diisopropylethylamine was added over 10 minutes, followed by stirring at the same temperature for 3 hours. At 0-7°C, 240 ml of ethyl acetate and 200 ml of water were added to the reaction liquid, and stirred for 10 minutes. The aqueous layer was separated, and the obtained organic layer was washed twice with 200 ml of 10% brine and once with 200 ml of water a...

Embodiment 1

[0101] The separation of embodiment 1 compound (1)

[0102] Cool 50 ml of a water-saturated ethyl acetate solution of compound (1) obtained in Reference Example 1 to -7°C and stir. At this point, water precipitates out in the form of ice. 4 ml of n-hexane was added over 13 minutes, followed by stirring at -7°C to obtain a (water-saturated ethyl acetate / n-hexane) mixed solution of compound (1). After 4 ml of n-hexane was added in full, solids began to precipitate after 1 minute. Ten minutes after solid precipitation started, the temperature was raised to 10° C., followed by stirring for another 30 minutes. 45 ml of n-hexane was added over 2.5 hours, followed by stirring at the same temperature for 2 hours. The obtained slurry was filtered, and the obtained solid content was dried under reduced pressure to obtain a compound (1) as a solid (7.5 g of pure content).

[0103] The crystallinity of the obtained solid was 52% (the crystallinity was measured by the crystallinity mea...

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Abstract

Disclosed is a process for production of p- nitrobenzyl (4R,5S,6S)-3-[[(3S,5S)-1-(p- nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3- pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo- 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, which is useful as an intermediate for the synthesis of meropenem. In the process, the isolation of the carboxylate can be completed within a short time, because the isolation of the carboxylate is achieved by mixing a solution of a rich solvent for the carboxylate with such an amount of a solution of a poor solvent for the carboxylate that the carboxylate is not precipitated as an oily material during the mixing.

Description

technical field [0001] The present invention relates to (4R, 5S, 6S)-3-[[(3S, 5S)-1-(p-nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]thio ]-6-[(1R)-1-Hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate p-nitrobenzyl ester The preparation method of the compound is as carbapenem antibiotic (carbapenem antibiotic) (4R, 5S, 6S)-3-[[(3S, 5S)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]sulfur Base]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (meropenem, meropenem, meropenem) synthetic intermediates are useful. Background technique [0002] According to the following general formula (1) [0003] [chemical 1] [0004] [0005] Represented (4R, 5S, 6S)-3-[[(3S, 5S)-1-(p-nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]sulfanyl] -p-nitrobenzyl 6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, As (4R,5S,6S)-3-[[(3S,5S)-5-(dimethylaminocarbonyl)-3-py...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/00
CPCC07D477/20
Inventor 西野敬太古贺照义
Owner KANEKA CORP
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