Hydrochloric Acid → HCID 61636743, compound
Reaction equation
[CH:1]1([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([O:14]C)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([OH:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of methyl 5-cyclohexyl-1,3-oxazole-4-carboxylate (6.40 g, 30.6 mmol) in methanol (370 mL) was added 1 M NaOH solution (92 mL). After being stirred at room temperature for 2 h, and at 50° C. for 1 h, the reaction mixture was cooled to 0° C., and then acidified with 1 M HCl solution. The mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting light yellow solid was triturated with hexane to give the title compound (5.29 g, 89%) as a white solid.
Workup
- waitat 50° C. for 1 h
- temperaturethe reaction mixture was cooled to 0° C.
- concentrationThe mixture was concentrated under reduced pressure
- customthe resulting residue was partitioned between ethyl acetate and water
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting light yellow solid was triturated with hexane
Sources & evidence
- ORD record
- ord-534ebc8d4e3a48b18bfc2766bb5e6d0f
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853215B2
Reaction notes
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