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Asymmetric catalytic hydrogenation process of synthesizing serial (2S,3R)-2 benzoyl aminomethyl-3-hydroxy butyrate compounds

A technology of benzamidomethyl and hydroxybutyrate, which is applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the limitations of industrial production and synthetic routes Long, cumbersome operation and other problems, to avoid high-pressure hydrogenation equipment, low cost, high yield effect

Active Publication Date: 2007-03-21
LUNAN PHARMA GROUP CORPORATION
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Problems solved by technology

There have been literature reviews on the synthesis process of (II), but most of the processes have disadvantages such as long synthetic route, low total yield, cumbersome operation, and high cost, thus limiting the industrial production of the compound of formula (II)

Method used

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  • Asymmetric catalytic hydrogenation process of synthesizing serial (2S,3R)-2 benzoyl aminomethyl-3-hydroxy butyrate compounds
  • Asymmetric catalytic hydrogenation process of synthesizing serial (2S,3R)-2 benzoyl aminomethyl-3-hydroxy butyrate compounds
  • Asymmetric catalytic hydrogenation process of synthesizing serial (2S,3R)-2 benzoyl aminomethyl-3-hydroxy butyrate compounds

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Embodiment Construction

[0017] The preparation method of the present invention is further described in detail below by way of examples.

[0018] 1. (2S, 3R)-2-benzoylaminomethyl-3-hydroxybutyric acid ethyl ester is the compound of formula (I), (2R, 3R)-2-benzoylaminomethyl-3-hydroxybutyrate Ethyl acid ester is the preparation of formula (IV) compound (R=Et):

[0019] Under nitrogen protection, the improved catalyst (R)-BINAP-RuBr under nitrogen protection 2 (1.0g) was transferred to a 2L round bottom flask, then degassed methanol (1200ml), ethyl 2-benzamidomethyl-3-oxobutanoate (III) (R=Et) (26.3g, 0.1 mol), a brown solution was obtained.

[0020] After replacing the nitrogen in the flask with hydrogen three times, the solution was vigorously stirred at 0.04kg / cm 2 under hydrogenation. To no longer consume hydrogen, about 24 hours. After purging the hydrogen in the flask with nitrogen, the reaction solution was filtered through a silica gel packing layer to remove the catalyst. After the filtra...

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Abstract

The present invention provides one process of preparing serial (2S, 3R)-2-benzoyl aminomethyl- 3-hydroxy butyrate compounds by means of improved chiral catalyst (R)-BINAP-RuBr2. The process of the present invention needs no use of high pressure hydrogenation apparatus, converts the catalytic side product into target product effectively, and has raised material converting rate and target product yield.

Description

technical field [0001] The present invention relates to the asymmetric synthesis of (2S, 3R)-2-benzamidomethyl-3-hydroxybutyrate represented by formula (I). The formula (I) compound prepared by the invention is the key intermediate (see formula 1) of industrial production formula (II) compound (abbreviated as 4-AA); the formula (II) compound can be used in carbapenem and penem drugs Used as an intermediate in the synthesis. [0002] Formula 1. Background technique [0003] Azetidinone compound 3R, 4R-3-[(1R)-tert-butyldimethylsiloxyethyl]-4-acetoxy-2-azetidinone (formula (II), referred to as 4-AA) is a key intermediate in the synthesis of new high-efficiency antibiotics carbapenems and penems, such as for the synthesis of carbapenem antibiotics imipenem, meropenem, faropenem and panipene Nan et al. [0004] The compound of formula (II) has 3 chiral centers, so there are 8 stereoisomers, which is very difficult to synthesize. There have be...

Claims

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Application Information

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IPC IPC(8): C07C233/83C07C231/12B01J31/24B01J31/30
Inventor 赵志全孙彬彭立增
Owner LUNAN PHARMA GROUP CORPORATION
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