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Improvement in the synthesis of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid 2-benzothiazolyl thioester

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Abstract

2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid 2-benzothiazolyl thioester(III), an important intermediate of the fourth generation cephalosporins, was efficiently synthesized by reacting 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid (I) with 2,2′-dibenzothiazole disulfide (II) in the presence of triphenylphosphine. Effects of reaction time, temperature, solvents, catalysts and feeding molar ratio on the yield and quality of products were investigated, and an improved procedure suitable for industrial production was established. Using 1,2-dichloroethane as solvent, triphenylphosphine as reducer, and triethylamine as catalyst, n(I): n(II): n(triphenylphosphine)51.0: 1.0: 1.0, the product was obtained at room temperature in 98.1% yield. The purity of the product without further purification is 98.7% determined by HPLC method. This procedure could be a suitable alternative to the traditional processes because of its easy handling, high yield and low cost.

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Authors and Affiliations

  1. School of Material Science and Technology, Beijing Institute of Technology, Beijing, 100081, China

    Shihao Gao, Chenghui Sun & Xinqi Zhao

  2. Pingdingshan No.55 Middle School, Pingdingshan, 467091, China

    Changquan Gao

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  1. Shihao Gao
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  2. Changquan Gao
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  3. Chenghui Sun
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  4. Xinqi Zhao
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Correspondence to Shihao Gao.

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Translated from Fine Chemicals, 2007, 24(8): 816–819 [译自:精细化工]

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Gao, S., Gao, C., Sun, C. et al. Improvement in the synthesis of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-methoxyiminoacetic acid 2-benzothiazolyl thioester. Front. Chem. Eng. China 2, 80–84 (2008). https://doi.org/10.1007/s11705-008-0017-0

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