Hydrochloric Acid → trans-2-{[(Cyanomethyl)amino]carbonyl}cyclopentanecarboxylic acid
Reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[C:12]([O:14]C)=[O:13])=[O:6])#[N:2].[OH-].[Na+].Cl>COCCOC.O>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[C:12]([OH:14])=[O:13])=[O:6])#[N:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Methyl trans-2-{[(cyanomethyl)amino]carbonyl}cyclopentanecarboxylate (1.08 g, 5.16 mmol) in ethylene glycol dimethyl ether (6.5 mL) was cooled to 0° C. 2.00 M aqueous sodium hydroxide (2.65 mL) was added and the reaction mixture was stirred at 0° C. for 3.5 h. The pH was adjusted to 5 with 2 M aqueous hydrochloric acid and the reaction mixture was diluted with water. The product was extracted into ethyl acetate, washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and concentrated to give trans-2-{[(cyanomethyl)amino]carbonyl}cyclopentanecarboxylic acid as a colorless solid.
Workup
- extractionThe product was extracted into ethyl acetate
- washwashed with saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-046aa25cd5954747ae29a7b2f1ada3db
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371747B2
Reaction notes
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