Reaction #324446

Reaction equation

KHSO4

title compound

3-[5-Chloro-2-(methoxycarbonyl-phenyl-methoxy)-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

NaOH

→

title compound

Yield 102.4%

3-[2-(Carboxy-phenyl-methoxy)-5-chloro-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

Yield 102.4%

Solvents

MeOH

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (2×)
2. 2
   WashThe combined organics were washed with brine
3. 3
   Otherdried

Procedure

To the title compound of Example 148 Step A (0.16 g, 0.36 mmol) in MeOH (3 mL) was added 1N NaOH (3 mL). After 18 h, the solution was acidified with 1N KHSO4 and extracted with EtOAc (2×). The combined organics were washed with brine and dried to give 0.16 g (>98%) of the title compound. 1H NMR (CDCl3): 8.56-8.19 (broad s, 1H), 7.55-7.51 (m, 2H), 7.41-7.36 (m, 3H), 6.85-6.84 (m, 2H), 6.54 (s, 1H), 5.55 (s, 1H), 4.88-4.83 (m, 1H), 4.29-4.24 (m, 2H), 4.06-3.97 (m, 2H), 1.44 (s, 9H).

Source