Hydrochloric Acid → 1-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid
Reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].Cl>[OH-].[Na+]>[CH2:12]([O:11][C:9]([N:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Azetidinecarboxylic acid (4.0 g, 39.6 mmol) was dissolved in 1N sodium hydroxide solution (40 mL) and cooled to 0° C. Benzyl chloroformate (5.9 mL, 41 mmol) was added followed by further 1N sodium hydroxide solution (41 mL) dropwise. The mixture was stirred vigorously for 16 hrs then made acidic with 2N hydrochloric acid. This suspension was extracted with dichloromethane (2×100 mL) and the extracts dried over MgSO4. Concentration yielded the title compound (9.3 g, 39.6 mmol, 100%).
Workup
- extractionThis suspension was extracted with dichloromethane (2×100 mL)
- dry with materialthe extracts dried over MgSO4
- concentrationConcentration
Sources & evidence
- ORD record
- ord-72dd5ef077534ed2aeeb4b7593185c01
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393858B2
Reaction notes
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