Industrial production process of 3R, 4R-3-[(1R)-tert-butyl dimethyl siloxane ethyl]-4-acetoxyl-2-azetinone

A technology of benzamidomethyl and alkyl, which is applied in the field of asymmetric synthesis, can solve the problems of great synthesis difficulty, high cost, cumbersome operation, etc., and achieve the effects of easy realization of reaction conditions, great competitive advantages, and high yield

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

[0005] 4-AA has 3 chiral centers, so there are 8 stereoisomers, which is very difficult to synthesize
There has been a review of the literature on the synthesis process of 4-AA, but most of the processes have the disadvantages of long synthetic route, low total yield, cumbersome operation, and high cost, thus limiting the industrial production of formula 4-AA

Method used

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  • Industrial production process of 3R, 4R-3-[(1R)-tert-butyl dimethyl siloxane ethyl]-4-acetoxyl-2-azetinone
  • Industrial production process of 3R, 4R-3-[(1R)-tert-butyl dimethyl siloxane ethyl]-4-acetoxyl-2-azetinone
  • Industrial production process of 3R, 4R-3-[(1R)-tert-butyl dimethyl siloxane ethyl]-4-acetoxyl-2-azetinone

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Embodiment Construction

[0018] The preparation method of the present invention is further described in detail below by way of examples.

[0019] 1. Preparation of (2S, 3R)-2-benzoylaminomethyl-3-benzoyloxybutyric acid ethyl ester, the compound of formula (V) (R=Et):

[0020] At 0° C., to (2S, 3S)-2-benzamidomethyl-3-hydroxybutyrate ethyl ester (IV) compound (8.48 g, 32 mmol; optical purity: 99.0%, HPLC) in tetrahydrofuran (200ml) solution was added successively triphenylphosphine (16.64g, 64mmol), benzoic acid (6.0g, 48mmol), diethyl azodicarboxylate (10.24ml, 64mmol), naturally warming up to room temperature, stirred at room temperature After 1 hour, the reaction mixture was distilled under reduced pressure, and the residual foam was the compound of formula V, which was directly used in the next step without treatment.

[0021] 2. The preparation of (2S, 3R)-2-aminomethyl-3-hydroxybutyric acid i.e. formula (VI) compound:

[0022] Dissolve V obtained in the above operation in 200ml of methanol, add...

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Abstract

The present invention provides 4-AA preparing process with (2S,3S)-2-benzoylaminomethyl-3- hydroxy butanoic ester, which is prepared with 2- benzoylaminomethyl-3-carbonyl butanoic ester, as material. The 4-AA preparing process has low cost, high yield, reaction condition suitable for industrial production and other advantages.

Description

technical field [0001] The present invention relates to 3R shown in formula (I), 4R-3-[(1R)-tert-butyldimethylsiloxyethyl]-4-acetoxy-2-azetidinone (abbreviated as 4 -Asymmetric synthesis of AA). The 4-AA prepared by the invention is a key intermediate for the industrial production of carbapenems and penems. [0002] [0003] Formula 1. Background technique [0004] Azetidinone compound 3R, 4R-3-[(1R)-tert-butyldimethylsiloxyethyl]-4-acetoxy-2-azetidinone (formula (I), 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. [0005] 4-AA has 3 chiral centers, so there are 8 stereoisomers, which is very difficult to synthesize. There have been literature reviews on the synthesis process of 4-AA, but most of the processes have disadvantages such as long synthetic route, lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/10C12R1/85
Inventor 赵志全孙彬彭立增
Owner LUNAN PHARMA GROUP CORPORATION
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