Conversion of Acylamidopenicillins to Phosphoramidopenicillins, and Removal of Their Phosphoryl Side Chain
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概要
- 論文の詳細を見る
On sequential treatment of benzylpenicillanates (1) or their sulfoxides (7) with phosphorus pentachloride, methanol, and sodium bicarbonate or dimethylaniline, 6-(dimethylphosphoramido) penicillins (5) or their sulfoxides (8) were obtained. 6-(Dimethylphosphoramido) penicillin sulfoxides (8) were rearranged thermally to their corresponding desacetoxycephalosporins (10). The dimethylphosphoryl group of 7-(dimethylphosphoramido) desacetoxycephalosporins (10) was removed by either a 85% phosphoric acid or polyphosphoric acid, which caused the degradation of β-lactam ring in 6-(dimethylphosphoramido) penicillins (5) and their sulfoxides (8). The dimethylphosphoryl group of penicillins and desacetoxycephalosporins was also removed by phosgene and pyridine to give 6-isocyanatopenicillins (16) and 7-isocyanatodesacetoxycephalosporins (15), respectively.
- 公益社団法人日本薬学会の論文
- 1976-12-25
著者
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中込 孟也
Research Department, Pharmaceutical Division, Sumitomo Chemical Co., Ltd.
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中込 孟也
Research And Development Center Pharmaceuticals Division Sumitomo Chemical Co. Ltd.
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福村 正孝
Research and Development Center, Pharmaceuticals Division, Sumitomo Chemical Co., Ltd.
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半間 範隆
Research and Development Center, Pharmaceuticals Division, Sumitomo Chemical Co., Ltd.
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半間 範隆
Research And Development Center Pharmaceuticals Division Sumitomo Chemical Co. Ltd.
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福村 正孝
Research And Development Center Pharmaceuticals Division Sumitomo Chemical Co. Ltd.
関連論文
- Synthesis of Pyridazine Derivatives. XII. Reaction of Amino-3 (2H) pyridazinone Derivatives with Tosyl Chloride
- Synthesis of Pyridazine Derivatives. XI. Synthesis of N^1-4-Pyridazinylsulfanilamide Derivatives
- Synthesis of Pyridazine Derivatives. XIII. Synthesis of N^1-(2-methyl-3-oxo-2,3-dihydro-4-pyridazinyl)-sulfanilamide Derivatives.
- Conversion of Acylamidopenicillins to Phosphoramidopenicillins, and Removal of Their Phosphoryl Side Chain
- Synthesis of Pyridazine Derivatives. XIV. On the Methylation of 4-Amino-3 (2H) pyridazinone Derivatives
- Synthesis of Pyridazine Derivatives. IX. Nitration of 3,4-Dimethylpyridazine N-Oxide Derivatives.
- Synthesis of Pyridazine Derivatives. VIII. N-Oxidation of 3,4-Dimethylpyridazine Derivatives.
- Bemerkung zur Nitrierung des 1,2,3,4-Tetrahydroisochinolins und seiner Derivate.
- Uber die Umlagerung von 5-Nitroisochinolin-N-Oxyd mittels Tosylchlorids.