Ethanol → ((4-Chloro-benzyl)-{1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carbonyl}-amino)-acetic acid

HRID 408601Notes

Reaction equation

C[O:2][C:3](=[O:32])[CH2:4][N:5]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:6]([C:8]1([CH3:23])[CH2:11][CH2:10][N:9]1[C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1)=[O:7].CCO.[OH-].[Na+]>CO>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]([C:8]2([CH3:23])[CH2:11][CH2:10][N:9]2[C:12](=[O:22])[CH2:13][C:14]2[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=2)=[O:7])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of ((4-chloro-benzyl)-{1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carbonyl}-amino)-acetic acid methyl ester, compound 48 (1 eq.) in either EtOH or MeOH was added aqueous NaOH (2N) (2 eq.). The reaction was stirred at 20° C. for 2 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 aqueous HCl (2N) and thoroughly extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated to afford ((4-chloro-benzyl)-{1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carbonyl}-amino)-acetic acid.

Workup

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

Sources & evidence

ORD record: ord-1d83123723404f37b8e07317dd79788d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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