Реакция #678305

Уравнение реакции

N-hydroxy-phtalimide

N,N′-diisopropylcarbodiimide

bimatoprost

NaHSO4

→

white crystalline material

Выход 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

Выход 58.4%

Растворители

THF

tert-butyl methyl ether

Условия реакции

Обработка

1. 1
   ДругоеThe phases are separated
2. 2
   Промывкаthe organic phase is washed with 1N NaHCO3 solution
3. 3
   Экстракцияthe aqueous-alkaline phase is extracted with TBME
4. 4
   СушкаThe united organic phase is dried over Na2SO4
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated
7. 7
   ДругоеThe residue is crystallized from hexane

Методика

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.

Источник