반응 #56580

반응 방정식

penicillin V

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

1,3-dicyclohexylcarbodiimide

→

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

용매

hexane

dichloromethane

반응 조건

후처리

1. 1
   여과filtered
2. 2
   농축concentrated to dryness
3. 3
   세척The residue was washed with hexane (3×50 ml)
4. 4
   기타to remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
5. 5
   세척washed with water (100 ml)
6. 6
   기타dried
7. 7
   workup.ADDITIONThe ether solution was diluted with hexane (125 ml)
8. 8
   여과the solution filtered through a bed of silica (4 cm×4 cm)
9. 9
   농축The filtrate was concentrated

실험 절차

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([phenoxyacetyl)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.

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