Hydrochloric Acid → HCID 86729748, compound
Reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[O:8])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[CH2:22](I)[CH3:23].[OH-].[Na+].Cl>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:22][CH3:23])=[O:8])=[CH:18][CH:19]=1)#[N:2]Participants
Conditions
- Temperature
- 60 °C
Procedure
To a solution of the compound obtained in Step 1 (200 mg, 0.77 mmol) in DMF (4 mL) were added sodium hydride (50% oil, 111 mg, 2.31 mmol) and ethyl iodide (0.093 mL, 1.15 mmol) at room temperature, and the mixture was stirred at 60° C. for 14 hr. To the reaction solution was added 1N aqueous sodium hydroxide solution (3 mL, 3.00 mmol), and the mixture was stirred at 60° C. for additional 2 hr. The reaction solution was cooled, and neutralized with 1N hydrochloric acid. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure to give 4-(4-cyano-N-ethylbenzamido)butanoic acid (0.23 g, 0.76 mmol, 98.7%) as a crude product.
Workup
- stirringthe mixture was stirred at 60° C. for additional 2 hr
- temperatureThe reaction solution was cooled
- extractionThe reaction mixture was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- customdried
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-e3b1ff01c1f34315a9017eb703a629fc
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120776B2
Reaction notes
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