반응 #62546

반응 방정식

4-bromo-methyl-5-methyl-1,3-dioxolene-2-one

HCl

7-formamido-3-(1,2,4-thiadiazol-4-yl)thiomethyl-3-cephem-4-carboxylic acid

propylene oxide

→

title compound

(5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl 7-formamido-3-(1,2,4-thiadiazol-4-yl)thiomethyl-3-cephem-4-carboxylate

용매

EtOAc

DMF

반응 조건

후처리

1. 1
   기타The EtOAc layer was separated
2. 2
   세척washed successively with aq HCl (pH 3) (70 ml×2), 10% K2HPO4 buffer (pH 7) (70 ml×2) and saturated aq NaCl (50 ml)
3. 3
   건조The EtOAc solution was dried (MgSO4)
4. 4
   농축concentrated in vacuo
5. 5
   기타The residue was triturated with ether (300 ml)
6. 6
   여과the resulting precipitate was filtered

실험 절차

A suspension of 7-formamido-3-(1,2,4-thiadiazol-4-yl)thiomethyl-3-cephem-4-carboxylic acid (1.07 g, 3 mmole), KHCO3 (1.0 g, 10 mmole) and propylene oxide (1 ml) in DMF (5 ml) was cooled to 5° C. and treated with 4-bromo-methyl-5-methyl-1,3-dioxolene-2-one (0.87 g, 4.5 mmole). After stirring at 5° C. for 5 hr, the reaction mixture was poured into a mixture of aq HCl (pH 3) (70 ml) and EtOAc (250 ml). The EtOAc layer was separated and washed successively with aq HCl (pH 3) (70 ml×2), 10% K2HPO4 buffer (pH 7) (70 ml×2) and saturated aq NaCl (50 ml). The EtOAc solution was dried (MgSO4) and concentrated in vacuo. The residue was triturated with ether (300 ml) and the resulting precipitate was filtered to give the title compound ( 0.45 g).

출처