반응 #55555

반응 방정식

7-amino-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

trimethylsilylacetamide

bis(trimethylsilyl)acetamide

phosphoryl chloride

2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetic acid

→

7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

수율 62.6%

용매

ethyl acetate

dimethylformamide

반응 조건

실험 절차

A solution of 7-amino-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (4.6 g), trimethylsilylacetamide (7.86 g) and bis(trimethylsilyl)acetamide (4.0 g) in ethyl acetate (50 ml) and a solution of dimethylformamide (0.804 g), phosphoryl chloride (1.69 g) and 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 12.3 g) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 4.2 g).

출처