Reaktion #56580

Reaktionsgleichung

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

Lösungsmittel

hexane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Einengenconcentrated to dryness
3. 3
   WaschenThe residue was washed with hexane (3×50 ml)
4. 4
   Sonstigeto remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
5. 5
   Waschenwashed with water (100 ml)
6. 6
   Sonstigedried
7. 7
   workup.ADDITIONThe ether solution was diluted with hexane (125 ml)
8. 8
   Filtrationthe solution filtered through a bed of silica (4 cm×4 cm)
9. 9
   EinengenThe filtrate was concentrated

Vorschrift

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.

Quelle