反応 #4599

反応方程式

morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

pyridine

phosgene

→

morpholinoethyl (E)-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate

溶媒

benzene

benzene

反応条件

後処理

1. 1
   ろ過the precipitate filtered off
2. 2
   その他solvent removed from the filtrate under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue is dissolved in 5 ml of tetrahydrofuran and to this solution
4. 4
   workup.ADDITIONis added dropwise a solution of ammonia in tetrahydrofuran until the reaction
5. 5
   workup.ADDITIONThe mixture is poured into water
6. 6
   抽出extracted with ethyl acetate
7. 7
   乾燥The organic solution is dried over magnesium sulfate
8. 8
   その他evaporated to an oil which
9. 9
   その他is chromatographed on silica gel
10. 10
    洗浄eluting with a 50:1 mixture of dichloromethane and methanol
11. 11
    workup.STIRRINGThe purified product is stirred with a mixture of ether and hexane
12. 12
    ろ過filtered

実験手順

To a solution of 500 mgs of morpholinoethyl (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate in 10 ml of benzene cooled in an ice bath is added 0.1 ml of pyridine and 6 ml of a 12.5% solution of phosgene in benzene. The solution is stirred at 25° C. overnight, the precipitate filtered off and solvent removed from the filtrate under reduced pressure. The residue is dissolved in 5 ml of tetrahydrofuran and to this solution is added dropwise a solution of ammonia in tetrahydrofuran until the reaction is complete. The mixture is poured into water and extracted with ethyl acetate. The organic solution is dried over magnesium sulfate and evaporated to an oil which is chromatographed on silica gel, eluting with a 50:1 mixture of dichloromethane and methanol. The purified product is stirred with a mixture of ether and hexane and filtered giving morpholinoethyl (E)-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate.

出典