Реакция #56580

Уравнение реакции

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

Растворители

hexane

dichloromethane

Условия реакции

Обработка

1. 1
   Фильтрацияfiltered
2. 2
   Концентрированиеconcentrated to dryness
3. 3
   ПромывкаThe residue was washed with hexane (3×50 ml)
4. 4
   Другоеto remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
5. 5
   Промывкаwashed with water (100 ml)
6. 6
   Другоеdried
7. 7
   workup.ADDITIONThe ether solution was diluted with hexane (125 ml)
8. 8
   Фильтрацияthe solution filtered through a bed of silica (4 cm×4 cm)
9. 9
   КонцентрированиеThe filtrate was concentrated

Методика

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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