Ethanol → 1-[2-(3,5-Dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid

HRID 408596

Reaction equation

C([O:3][C:4]([C:6]1([CH3:21])[CH2:9][CH2:8][N:7]1[C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)=[O:5])C.CCO.[OH-].[Na+]>CO>[CH3:19][C:14]1[CH:13]=[C:12]([CH2:11][C:10]([N:7]2[CH2:8][CH2:9][C:6]2([CH3:21])[C:4]([OH:5])=[O:3])=[O:20])[CH:17]=[C:16]([CH3:18])[CH:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid ethyl ester, Intermediate 94 (1 eq.) in either EtOH or MeOH was added aqueous NaOH (2N) (2 eq.). The reaction was stirred at 20° C. for 6 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 neutralized by addition of aqueous HCl (2N) and thoroughly extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid.

Workup

customThe solvent was removed under reduced pressure
customthe crude was partitioned between water and EtOAc
additionthe aqueous layer was neutralized by addition of aqueous HCl (2N)
extractionthoroughly extracted with EtOAc
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e2ffb32b6f0e4605973395909221a88f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Linked notes

Loading…