反应 #2467913

反应方程式

penicillin V

1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

1,3-dicyclohexylcarbodiimide

→

1-(3,3-dimethyl-7-oxo-6([phenoxy acetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-oyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane

溶剂

hexane

dichloromethane

反应条件

后处理

1. 1
   过滤filtered
2. 2
   浓缩concentrated to dryness
3. 3
   洗涤The residue was washed with hexane (3×50 ml)
4. 4
   其他to remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
5. 5
   洗涤washed with water (100 ml)
6. 6
   其他dried
7. 7
   workup.ADDITIONThe ether solution was diluted with hexane (125 ml)
8. 8
   过滤the solution filtered through a bed of silica (4 cm×4 cm)
9. 9
   浓缩The filtrate was concentrated

实验过程

A mixture of penicillin V (1 g, 2.9 mmol), 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (860 mg, 2.6 mmol), 1,3-dicyclohexylcarbodiimide (620 mg, 3 mmol) and 4-(N,N-dimethylamino)pyridine (catalytic amount) in dichloromethane (30 ml) was stirred overnight at room temperature. The reaction mixture was diluted with hexane (50 ml), filtered and concentrated to dryness. The residue was washed with hexane (3×50 ml) to remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane. The semisolid residue was disolved in diethyl ether (150 ml), washed with water (100 ml) and dried. The ether solution was diluted with hexane (125 ml) and the solution filtered through a bed of silica (4 cm×4 cm). The filtrate was concentrated, yielding 1-(3,3-dimethyl-7-oxo-6([phenoxy acetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-oyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane as a viscous colourless oil.

来源