Reaction #324432

Reaction equation

title compound

5-Bromomethyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester

Cs2CO3

NaOH

3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

→

title compound

3-[2-(4-Carboxy-5-trifluoromethyl-furan-2-ylmethoxy)-5-chloro-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

Solvents

DMF

EtOAc

Conditions

Workup

1. 1
   OtherThe title compound was prepared
2. 2
   workup.ADDITIONwere added
3. 3
   WashThe organic layer was washed with 1N NaOH
4. 4
   Otherdried
5. 5
   OtherThe crude material was purified by RP HPLC

Procedure

The title compound was prepared as described in Example 1 Step D using 3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.50 mmol), the title compound of Step A (0.18 g, 0.60 mmol), Cs2CO3 (0.41 g, 1.2 mmol), KI (0.12 g, 0.70 mmol) in DMF, except upon completion of the reaction 1N NaOH and EtOAc were added. The organic layer was washed with 1N NaOH and dried. The crude material was purified by RP HPLC to provide the title compound. 1H NMR (CDCl3): 7.20-6.92 (m, 1H), 6.91-6.80 (m, 2H), 6.77-6.69 (m, 1H), 6.53 (d, J=2.1 Hz, 1H), 4.87 (s, 2H), 4.79-4.69 (m, 1H), 4.27-4.12 (m, 2H), 4.00-3.88 (m, 2H), 1.38 (s, 9H).

Source