Reaction #84051

Reaction equation

polymeric support resin

4-Hydroxy-2,3,5,6-tetrafluorobenzoic acid

1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride

N,N′-diisopropylcarbodiimide

→

polymer-bound title compound

(2-(1-Azabicyclo[2.2.2]oct-3-yl)acetoxy}-2,3,5,6-tetrafluorobenzoic acid

Solvents

DMF

Conditions

Workup

1. 1
   FiltrationThe resin is filtered off with suction
2. 2
   Washwashed twice each with 20 ml each of DMF, THF and DCM
3. 3
   Otherdried under high vacuum

Procedure

2 g of the polymeric support resin from Example 8A (loading about 1.36 mmol/g, 2.72 mmol) are suspended in 20 ml of DMF and shaken with 1.23 g (5.98 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride and 130 mg (1.09 mmol) of DMAP for 10 min. Then 1.06 ml (6.80 mmol) of N,N′-diisopropylcarbodiimide are added, and the mixture is shaken overnight. The resin is filtered off with suction, washed twice each with 20 ml each of DMF, THF and DCM and dried under high vacuum. 2.318 g of the polymer-bound title compound are obtained.

Source