반응 #213937

반응 방정식

phosphorus oxychloride

2-[2-(2-thienyl)acetoxyimino]-2-(3-hydroxyphenyl)acetic acid

7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

bis(trimethylsilyl)acetamide

→

7-[2-(2-(2-thienyl)acetoxyimino)-2-(3-hydroxyphenyl)acetamido]-3-(1methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

수율 71.5%

용매

ethyl acetate

Water

ethyl acetate

methylene chloride

Dimethylformamide

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONwas added the above obtained solution
2. 2
   workup.STIRRINGThen the reaction mixture was stirred for 1 hour at the same temperature
3. 3
   workup.STIRRINGthe mixture was stirred for 10 minutes
4. 4
   기타The ethyl acetate layer was separated
5. 5
   추출The aqueous layer was extracted with ethyl acetate
6. 6
   세척The extract was washed with a saturated aqueous solution of sodium chloride
7. 7
   기타dried
8. 8
   workup.DISTILLATIONThe solvent was distilled off
9. 9
   여과collected by filtration
10. 10
    세척washed

실험 절차

Dimethylformamide (0.4 g.), phosphorus oxychloride (0.81 g.), methylene chloride (20 ml.), ethyl acetate (10 ml.) and 2-[2-(2-thienyl)acetoxyimino]-2-(3-hydroxyphenyl)acetic acid (syn isomer) (1.68 g.) were treated in a manner as in example 1(B) to give an ethyl acetate solution. On the other hand, 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.64 g.) and bis(trimethylsilyl)acetamide (3.55 g.) were dissolved in ethyl acetate (20 ml.) and stirred at -20° C., to which was added the above obtained solution. Then the reaction mixture was stirred for 1 hour at the same temperature. Water was added thereto and the mixture was stirred for 10 minutes. The ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate. Two ethyl acetate layers were combined. The extract was washed with a saturated aqueous solution of sodium chloride and dried. The solvent was distilled off. The residue was pulverized with a mixed solution of diisopropylether and ether, collected by filtration and washed to give 7-[2-(2-(2-thienyl)acetoxyimino)-2-(3-hydroxyphenyl)acetamido]-3-(1methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.2 g.).

출처