1-[(4-Fluorobenzoyl)amino]cyclohexanecarboxylic acid → 2-(4-Fluorophenyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one
Reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=O)=[CH:4][CH:3]=1>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[O:16][C:15](=[O:17])[C:9]3([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[N:8]=2)=[CH:4][CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
After a suspension of 13.3 g (50 mmol) of 1-[(4-fluorobenzoyl)amino]cyclohexanecarboxylic acid in 30 ml of acetic anhydride was stirred at 100° C. for 30 minutes, the reaction solution was concentrated under reduced pressure. Toluene was added to the residue, and the mixture was washed with water, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine. After the organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 8.5 g (69%) of the title compound.
Workup
- concentrationthe reaction solution was concentrated under reduced pressure
- additionToluene was added to the residue
- washthe mixture was washed with water
- dry with materialAfter the organic layer was dried with anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-0b553825e7b743cb99245ba8d4ddb88c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829209B2
Reaction notes
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