Synthesis of (2S,3S)-2-benzoyl aminometh-3-hydroxy-butyrate ester series compound by asymmetric yeast cell

A technology of benzoylaminomethyl and hydroxybutyrate, which is applied in the field of biological asymmetric synthesis of 2-benzoylaminomethyl-3-hydroxybutyrate, can solve the problem of high product yield and by-products Waste, environmental pollution and other problems, to achieve the effect of easy realization of reaction conditions, great competitive advantage, and simple operation

Active Publication Date: 2010-10-13
LUNAN PHARMA GROUP CORPORATION
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Problems solved by technology

US4927507 provides a method of utilizing baker's yeast to reduce α-benzamidomethyl-ethyl acetoacetate, the reaction product is (2S, 3S)-2-benzamidomethyl-3-hydroxybutyric acid Ethyl ester and (2R,3S)-2-benzamidomethyl-3-hydroxybutyrate ethyl ester were separated by silica gel chromatography and the purity of the corresponding isomers was tested, but they were directly used in bread Yeast, practice has proved that if the yeast is used directly, the separation of the product is often difficult, but the use of solid-loaded yeast can be easy to operate, and the product yield is high, and no (2R, 3S) configuration by-products are converted into ( 2S, 3S) configuration products, resulting in a large amount of waste of by-products, polluting the environment and increasing production costs

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  • Synthesis of (2S,3S)-2-benzoyl aminometh-3-hydroxy-butyrate ester series compound by asymmetric yeast cell
  • Synthesis of (2S,3S)-2-benzoyl aminometh-3-hydroxy-butyrate ester series compound by asymmetric yeast cell
  • Synthesis of (2S,3S)-2-benzoyl aminometh-3-hydroxy-butyrate ester series compound by asymmetric yeast cell

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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, 3S)-2-benzoylaminomethyl-3-hydroxybutyric acid ethyl ester is the compound of formula (I), (2R, 3S)-2-benzoylaminomethyl-3-hydroxybutyrate Ethyl acid ester is the preparation of formula (V) compound (R=Et):

[0019] Add tap water (2500ml), sucrose (600g), baker's yeast (100g, Angel Yeast, purchased in a supermarket) successively in a 5-liter three-necked round-bottomed flask equipped with a bubbler and a thermometer, and stir the mixture slightly (120r / min) .

[0020] After 1 hr, make the generated CO 2 Gas escapes at a rate of about 1 to 2 bubbles / second. Then 2-benzamidomethyl-3-carbonylbutyrate (III, 35 g) was added thereto, and the mixture was stirred at 33˜36° C. for 24 hours.

[0021] Sucrose (150 g) was dissolved in 500 ml of tap water and added to the reaction mixture, stirring was continued at 33-36° C., and the reaction was monitored by...

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Abstract

Synthesis of (2S,3S)-2-benzoyl-aminomethyl-3-hydroxy-butyrate ester series compound by yeast cell asymmetry is carried out by taking baker yeast as raw material and converting to obtain the final product by one-step biological method. It's effective and efficient and has better substrate percent conversion.

Description

technical field [0001] The present invention relates to the bioasymmetric synthesis of (2S, 3S)-2-benzamidomethyl-3-hydroxybutyrate represented by formula (I). The compound of formula (I) prepared by the invention is the key intermediate for industrial production of the compound of formula (II) (abbreviated as 4-AA); the compound of formula (II) can be used in the synthesis of carbapenems and penems Intermediate (see Formula 1). [0002] 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 been literature reviews on the synthes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/00C12R1/85
Inventor 赵志全彭立增孙彬
Owner LUNAN PHARMA GROUP CORPORATION
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