Hydrochloric Acid → (2S)-1-[(1,5-dimethylpyrazol-3-yl)carbonyl]azetidine-2-carboxylic acid
Reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9]([C:11]1[CH:15]=[C:14]([CH3:16])[N:13]([CH3:17])[N:12]=1)=[O:10])=[O:4].[Li+].[OH-].Cl>CO.O>[CH3:17][N:13]1[C:14]([CH3:16])=[CH:15][C:11]([C:9]([N:6]2[CH2:7][CH2:8][C@H:5]2[C:3]([OH:4])=[O:2])=[O:10])=[N:12]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2S)-methyl-1-[(1,5-dimethylpyrazol-3-yl)carbonyl]azetidine-2-carboxylate (398.4 mg, 1.68 mmol) in methanol (12 mL) was added 1N LiOH in water (3.1 mL) at about 0° C. The mixture was stirred under argon at about 0° C. for about 30 minutes and then at about room temperature overnight. The pH was adjusted to about pH 1 by adding 1 N HCl and then the mixture was diluted with water and extracted with dichloromethane. The organic layers were washed with brine, dried over sodium sulfate and then concentrated to give 315.2 mg (84% yield) of the product as a white solid. 1H NMR (CDCl3) δ 2.32 (s, 3H); 2.49-3.89 (series of m, 2H); 3.84 (s, 3H); 4.40-4.71 (series of m, 2H); 5.20 (t, 1H, J=7.7); 6.57 (s, 1H).
Workup
- customat about room temperature
- customovernight
- extractionextracted with dichloromethane
- washThe organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-43b004a31c854e10bf3d173586423f22
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06544976B1
Reaction notes
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