Sodium Hydroxide → 1-[(Tert-butoxy)carbonyl]-2-methylazetidine-2-carboxylic acid
Reaction equation
CC[O:3][C:4]([C:6]1([CH3:17])[CH2:9][CH2:8][N:7]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:5].[OH-].[Na+]>CCO>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:6]1([CH3:17])[C:4]([OH:5])=[O:3])=[O:11])([CH3:16])([CH3:14])[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 2-methyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester, Intermediate 11 (1 eq.) in EtOH was added an aqueous solution of 2N NaOH (2 eq.). The reaction was stirred at 20° C. for 15 h. The solvent was removed under reduced pressure and the crude was partitioned between water and EtOAc. The organic layer was discarded and the aqueous layer was acidified by addition of a solution of citric acid 10% in water until pH=3 and thoroughly extracted by EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford 2-methyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester.