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

참여 물질

역할	이름	HCID	투입량
반응물	Phosphorus oxychloride	HCID 24813	—
반응물	Acetamide, 2-(trimethylsilyl)-	HCID 357676	—
반응물	Bistrimethylsilylacetamid	HCID 11708267	—
반응물	(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid	HCID 12941984	—
반응물	2-(2-Formamidothiazol-4-yl)-2-(2-methylthiazol-4-ylmethoxyimino)acetic acid	HCID 53718792	—
용매	Water	HCID 962	—
용매	Dimethylformamide	HCID 6228	—
용매	Ethyl Acetate	HCID 8857	—
생성물	7-[2-(2-Formamidothiazol-4-yl)-2-(2-methylthiazol-4-yl methoxyimino)acetamido]-3-cephem-4-carboxylic acid	HCID 131712338	61.8%

반응 단계

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 ethyl acetate (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 ethyl 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.).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US04372952
출처 데이터셋	uspto-grants-1983_02
ORD ID	ord-1a83baf7bdea44bc8af9078753bd55f2
출처 메모	uspto-grants-1983_02