تفاعل #56580

معادلة التفاعل

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

المذيبات

hexane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   ترشيحfiltered
2. 2
   تركيزconcentrated to dryness
3. 3
   غسيلThe residue was washed with hexane (3×50 ml)
4. 4
   أخرىto remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
5. 5
   غسيلwashed with water (100 ml)
6. 6
   أخرىdried
7. 7
   workup.ADDITIONThe ether solution was diluted with hexane (125 ml)
8. 8
   ترشيحthe solution filtered through a bed of silica (4 cm×4 cm)
9. 9
   تركيزThe filtrate was concentrated

الإجراء التجريبي

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.

المصدر