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HRID 745420作成日:2026年10月26日

Phosphorus oxychloride → 7-[2-(2-Formamidothiazol-4-yl)-2-(2-methylthiazol-4-yl methoxyimino)acetamido]-3-cephem-4-carboxylic acid

https://huagongshe.com/reaction/745420

反応式

関与物質

役割名称HCID仕込み量
反応物Phosphorus oxychlorideHCID 24813—
反応物Acetamide, 2-(trimethylsilyl)-HCID 357676—
反応物BistrimethylsilylacetamidHCID 11708267—
反応物(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 12941984—
反応物2-(2-Formamidothiazol-4-yl)-2-(2-methylthiazol-4-ylmethoxyimino)acetic acidHCID 53718792—
溶媒WaterHCID 962—
溶媒DimethylformamideHCID 6228—
溶媒Methyl AcetateHCID 6584—
溶媒Ethyl AcetateHCID 8857—
生成物7-[2-(2-Formamidothiazol-4-yl)-2-(2-methylthiazol-4-yl methoxyimino)acetamido]-3-cephem-4-carboxylic acidHCID 13171233861.8%

反応手順

2-(2-Formamidothiazol-4-yl)-2-(2-methylthiazol-4-yl-methoxyimino)acetic acid (syn isomer, 0.50 g.), N,N-dimethylformamide (0.123 g.), phosphoryl chloride (0.259 g.) and ethylacetate (6 ml.) were treated in a similar manner to that of Example 1-(1) to give an activated acid solution. The solution and a solution of 7-amino-3-cephem-4-carboxylic acid (0.306 g.), trimethylsilylacetamide (1.03 g.), and bis(trimethylsilyl)acetamide (0.90 ml.) in methyl acetate (3 ml.) were treated in a similar manner to that of Example 1-(1). Water (10 ml.) was added to the resultant mixture, and the ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated in vacuo to give 7-[2-(2-formamidothiazol-4-yl)-2-(2-methylthiazol-4-yl methoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.48 g.)

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US04598147
出典データセットuspto-grants-1986_07
ORD IDord-768a7bc9acbc40e19fff191e7cc8578f
出典メモuspto-grants-1986_07