반응 #701314

반응 방정식

6-(triphenylmethylamino)-2,2-dimethyl-3-(N-furfurylcarbamoyl)penam

tetramethylguanidinium azide

phosgene

pyridine

→

6-(triphenylmethylamino)-2,2-dimethyl-3-(1-furfuryltetrazol-5-yl)penam

용매

water

chloroform

chloroform

chloroform

chloroform

반응 조건

후처리

1. 1
   기타The chloroform, and excess phosgene and pyridine, are then removed by evaporation in vacuo
2. 2
   workup.DISSOLUTIONthe residue is redissolved in 5 ml
3. 3
   workup.STIRRINGStirring
4. 4
   workup.WAITis continued for 15 minutes at ambient temperature
5. 5
   기타The chloroform layer is separated off
6. 6
   세척washed with water
7. 7
   건조dried (MgSO4)
8. 8
   기타Removal of the solvent
9. 9
   기타by evaporation in vacuo
10. 10
    기타leaves 3.37 g
11. 11
    기타absorbed onto a column of chromatographic silica gel
12. 12
    세척Elution of the column with chloroform
13. 13
    기타followed by evaporation of the appropriate fractions in vacuo

실험 절차

To a stirred solution of 3.05 g. (5.7 mmole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-furfurylcarbamoyl)penam, in 8 ml. of chloroform, at 0° C., is added 1.35 ml. (17 mmole) of pyridine, followed by 2.64 ml. of a 4.33 M solution of phosgene in chloroform. Stirring is then continued for 1 hour at 25° C. The chloroform, and excess phosgene and pyridine, are then removed by evaporation in vacuo, and the residue is redissolved in 5 ml. of chloroform. The solution is cooled to 0° C., and then 2.25 g. (14.4 mmole) of tetramethylguanidinium azide is added in several small portions. Stirring is continued for 15 minutes at ambient temperature, and then 20 ml. of chloroform, followed by 30 ml. of water, are added and the pH is adjusted to 6.5. The chloroform layer is separated off, washed with water, followed by brine, and then dried (MgSO4). Removal of the solvent by evaporation in vacuo leaves 3.37 g. of a dark-red foam. The foam is re-dissolved in a small volume of chloroform and absorbed onto a column of chromatographic silica gel. Elution of the column with chloroform, followed by evaporation of the appropriate fractions in vacuo, affords 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-furfuryltetrazol-5-yl)penam. The NMR spectrum of the product (CDCl3) shows absorptions at 7.40 ppm (m, 16H), 6.40 ppm (m, 2H), 5.50 ppm (s, 2H), 5.20 ppm (s, 1H), 4.90 ppm (m, 2H), 1.60 ppm (s, 3H), and 0.80 ppm (s, 3H).

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