Réaction #324432

Équation de réaction

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

Solvants

DMF

EtOAc

Conditions de réaction

Traitement

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

Mode opératoire

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