Reaktion #69728

Reaktionsgleichung

2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

EDC

HOBT

BOC piperazine

→

4-[2-(2,4-dihydroxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Ausbeute 102.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated under vacuum
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in ethyl acetate
3. 3
   Extraktionextracted twice with saturated NaHCO3
4. 4
   Waschenorganics washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigethen evaporated under vacuum
8. 8
   Sonstigepurified by flash column chromatography (80% EtOAc-P.E. as eluant)

Vorschrift

A solution of 2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid (Preparation D6) (0.5 g, 0.96 mmol), EDC (0.22 g, 1.15 mmol), HOBT (0.196 g, 1.15 mmol) and BOC piperazine (0.117 ml, 1.06 mmol) in DMF (10 ml) was stirred at room temperature for 48 hours, then evaporated under vacuum. The crude material was dissolved in ethyl acetate and extracted twice with saturated NaHCO3, organics washed with brine, dried (MgSO4), filtered then evaporated under vacuum and purified by flash column chromatography (80% EtOAc-P.E. as eluant) to give 0.5 g of 4-[2-(2,4-dihydroxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester. MS: [M+H]+ 688.

Quelle