반응 #215691

반응 방정식

benzyl (2S,3S)-1-(3,4-dimethoxybenzyl)-2-[1 (R),2-dihydroxyethyl]-4-oxo-3-azetidinecarbamate

1,1'-carbonyldiimidazole

→

pure product

수율 96.5%

Benzyl (2S,3S)-1-(3,4-dimethoxybenzyl)-2-[(R)-2-oxo-1,3-dioxolan-4-yl]-4-oxo-3-azetidine carbamate

수율 96.5%

용매

THF

반응 조건

후처리

1. 1
   온도under reflux for 4 hours
2. 2
   기타The THF was subsequently removed by concentration
3. 3
   세척washed once with 500 ml of 1N aqueous hydrochloric acid, twice with 1 l of water each time
4. 4
   건조once with 500 ml of saturated, aqueous sodium chloride solution and dried over magnesium sulphate with the addition of about 7 g of fuller's earth
5. 5
   기타The solvent was removed by concentration
6. 6
   기타After drying there

실험 절차

215.23 g (0.5 mol) of benzyl (2S,3S)-1-(3,4-dimethoxybenzyl)-2-[1 (R),2-dihydroxyethyl]-4-oxo-3-azetidinecarbamate were dissolved in 3 l of THF at the boiling temperature. 12.61 g (0.75 mol) of 1,1'-carbonyldiimidazole were added. The mixture was boiled under reflux for 4 hours. The THF was subsequently removed by concentration, the oily residue was taken up in 1.5 l of dichloromethane, washed once with 500 ml of 1N aqueous hydrochloric acid, twice with 1 l of water each time and once with 500 ml of saturated, aqueous sodium chloride solution and dried over magnesium sulphate with the addition of about 7 g of fuller's earth. The solvent was removed by concentration. After drying there were obtained without further purification 220.3 g (yield: 96%) of pure product. M.p.: 135°-136° C.

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