반응 #701313

반응 방정식

6-aminopenicillanic acid

4-methoxybenzylamine

ethyl chloroformate

triphenylmethyl chloride

→

6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-methylbenzyl]carbamoyl)penam

용매

chloroform

triethylamine

triethylamine

chloroform

반응 조건

후처리

1. 1
   기타is obtained (ca. 15 minutes)
2. 2
   workup.ADDITIONTo this solution is then added, portionwise over about 25 minutes
3. 3
   기타at ambient temperature
4. 4
   온도The solution is cooled to 0°-5° C.
5. 5
   온도being maintained between 4° and 9° C
6. 6
   workup.STIRRINGAfter a further 15 minutes of stirring
7. 7
   기타is injected into the reaction medium, below the surface of the solvent, at 4° to 9° C.
8. 8
   workup.WAITover a period of 30 minutes
9. 9
   workup.STIRRINGStirring
10. 10
    workup.WAITis continued for a further 30 minutes at 3° to 6° C., for 20 minutes while the reaction medium warms to 20° C
11. 11
    세척The reaction mixture is then washed with water
12. 12
    기타Finally, it is dried

실험 절차

To a stirred slurry of 86.4 g. (0.4 mole) of 6-aminopenicillanic acid in 600 ml. of anhydrous chloroform is added 111.2 ml. (0.8 mole) of triethylamine, and the mixture is stirred at ambient temperature until a clear solution is obtained (ca. 15 minutes). To this solution is then added, portionwise over about 25 minutes, 134.9 g. (0.44 mole), of 90% pure triphenylmethyl chloride, at ambient temperature. Stirring is continued for a further 64 hours, and then 5.6 ml. of triethylamine is added. The solution is cooled to 0°-5° C., and then an ice-cold solution of 38 ml. (0.4 mole) of ethyl chloroformate in 80 ml. of chloroform is added dropwise during 30 minutes with the reaction temperature being maintained between 4° and 9° C. After a further 15 minutes of stirring, 52.4 ml. (0.4 mole) of 4-methoxybenzylamine is injected into the reaction medium, below the surface of the solvent, at 4° to 9° C., and over a period of 30 minutes. Stirring is continued for a further 30 minutes at 3° to 6° C., for 20 minutes while the reaction medium warms to 20° C. The reaction mixture is then washed with water, followed by brine. Finally, it is dried using magnesium sulfate to give a chloroform solution of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-methylbenzyl]carbamoyl)penam

출처