Hydrochloric Acid → (2S)-1-(Benzyloxycarbonyl)azetidine-2-carboxylic acid
Reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[O:4].CCOCC.[Li+].[OH-].Cl>O.CO>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C@H:5]1[C:3]([OH:4])=[O:2])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2S)-methyl-1-(benzyloxycarbonyl)azetidine-2-carboxylate (0.78 g, 3.12 mmol) in a 1:1 mixture of ether:methanol (25.0 mL) was added 1N LiOH in water (5.8 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 1N HCl, then the mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give 0.78 g (99% yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 2.45-2.63 (br, 2H); 4.00 (t, 2H, J=7.7); 4.77-4.90 (br, 1H); 5.16 (s, 2H); 7.37 (s, 5H).
Workup
- customat about room temperature
- customovernight
- extractionextracted with dichloromethane
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0679f02e1fa54c67902d9c16f0e8a16e
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06544976B1
Reaction notes
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