반응 #348432

반응 방정식

water

2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]aminopenam-3-carboxylate

sodium bicarbonate

5-methyl-1,3,4-thiadiazole-2-thiol

→

2,2,2-trichloroethyl 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-2-methyl-6-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]aminopenam-3-carboxylate

수율 10.8%

용매

formamide

formamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The extract was washed with 5% sodium bicarbonate aqueous solution
4. 4
   건조with water, dried
5. 5
   workup.DISTILLATIONafter which the solvent was distilled off
6. 6
   세척eluted with chloroform
7. 7
   기타The eluate was separated into fractions of each 50 ml
8. 8
   기타after collecting the fractions of the fifteenth and sixteenth, the solvent
9. 9
   workup.DISTILLATIONwas distilled off

실험 절차

A solution of 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]aminopenam-3-carboxylate (3.6 g) in formamide (40 ml) was added to a solution of sodium bicarbonate (0.66 g) and 5-methyl-1,3,4-thiadiazole-2-thiol (1.1 g) in formamide (60 ml) under ice-cooling, after which the mixture was stirred for 4.5 hours at the same temperature. After the reaction was completed, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 5% sodium bicarbonate aqueous solution and then with water, dried, after which the solvent was distilled off. The oily residue was subjected to column chromatography on silica gel (110 g) and eluted with chloroform. The eluate was separated into fractions of each 50 ml and after collecting the fractions of the fifteenth and sixteenth, the solvent was distilled off to give oily 2,2,2-trichloroethyl 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-2-methyl-6-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]aminopenam-3-carboxylate (0.42 g).

출처