반응 #56571

반응 방정식

2-methyl-7-[2-(2-formylaminothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid

2-methyl-7-[2-(2-formylimino-2,3-dihydrothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid

sodium bicarbonate

sodium acetate trihydrate

O-methylhydroxylamine hydrochloride

sodium bicarbonate

→

2-methyl-7-[2-methoxyimino-2-(2-formylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 2 hours at 48° to 50° C
2. 2
   온도After cooling the reaction mixture
3. 3
   workup.DISSOLUTIONin order to dissolve the precipitated insoluble material
4. 4
   기타The aqueous layer was separated
5. 5
   세척washed with ethyl acetate
6. 6
   추출extracted with ethyl acetate
7. 7
   추출The ethyl acetate extract
8. 8
   세척was washed with a saturated aqueous sodium chloride solution
9. 9
   건조dried over magnesium sulfate
10. 10
    농축concentrated
11. 11
    여과collected by filtration
12. 12
    기타dried

실험 절차

To a suspension of 2-methyl-7-[2-(2-formylaminothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, which can be represented as 2-methyl-7-[2-(2-formylimino-2,3-dihydrothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, (792 mg.) in water (20 ml.) was added sodium bicarbonate (168 mg.) with stirring. To thus obtained solution were added sodium acetate trihydrate (272.2 mg.) and O-methylhydroxylamine hydrochloride (334 mg.), and the mixture was stirred for 2 hours at 48° to 50° C. After cooling the reaction mixture, a saturated aqueous sodium bicarbonate solution (10 ml.) and ethyl acetate (15 ml.) were added thereto in order to dissolve the precipitated insoluble material. The aqueous layer was separated, washed with ethyl acetate, adjusted to pH 1 with 2 N hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate extract was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated. The residue was pulverized in diethyl ether, collected by filtration and then dried to give 2-methyl-7-[2-methoxyimino-2-(2-formylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-methoxyimino-2-(2-formylimino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-carboxylic acid (syn isomer), (505 mg.). This compound was recrystallized from methanol to give white crystals of the pure object compound.

출처