Réaction #678305

Équation de réaction

N-hydroxy-phtalimide

N,N′-diisopropylcarbodiimide

bimatoprost

NaHSO4

→

white crystalline material

Rendement 58.4%

7-[3,5-Dihydroxy-2-(3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-5-heptenoic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

Rendement 58.4%

Solvants

THF

tert-butyl methyl ether

Conditions de réaction

Traitement

1. 1
   AutreThe phases are separated
2. 2
   Lavagethe organic phase is washed with 1N NaHCO3 solution
3. 3
   Extractionthe aqueous-alkaline phase is extracted with TBME
4. 4
   SéchageThe united organic phase is dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated
7. 7
   AutreThe residue is crystallized from hexane

Mode opératoire

2 g of bimatoprost acid is dissolved in 20 ml of THF and to this solution are added at room temperature 1 g of N-hydroxy-phtalimide and 1 ml of N,N′-diisopropylcarbodiimide. The reaction mixture is stirred for 2 hours and then poured onto they mixture of 1N NaHSO4 solution and tert-butyl methyl ether (TBME). The phases are separated, the organic phase is washed with 1N NaHCO3 solution and the aqueous-alkaline phase is extracted with TBME. The united organic phase is dried over Na2SO4, filtered and evaporated. The residue is crystallized from hexane:acetone mixture to obtain 1.5 g white crystalline material.

Source