Hydrochloric Acid → 1-(3-Hydroxy-4-methoxy-benzoylamino)-4-trifluoromethyl-cyclohexanecarboxylic Acid Methyl Ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25]C(=O)C)[CH:18]=2)[CH2:10][CH2:9][CH:8]([C:11]([F:14])([F:13])[F:12])[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].CC(=O)OCC.Cl>CO>[CH3:1][O:2][C:3]([C:5]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([OH:25])[CH:18]=2)[CH2:6][CH2:7][CH:8]([C:11]([F:14])([F:13])[F:12])[CH2:9][CH2:10]1)=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
105 mg of 1-(3-Acetoxy-4-methoxy-benzoylamino)-4-trifluoromethyl-cyclohexanecarboxylic acid methyl ester and 7.0 mg of K2CO3 were stirred in 4 ml of anhydrous methanol for 1 h at room temperature. Then, 10.4 mg of K2CO3 were added and stirring was continued for 2 h at room temperature. 10 ml of EA and 10 ml of a 1N aqueous HCl-solution were then added. The layers were separated and the aqueous layer was extracted twice using 10 ml of EA each. The combined organic layers were washed twice using 10 ml of a saturated aqueous NaHCO3-solution, once using 10 ml of a 1N aqueous HCl-solution, and once using a 10 ml of a saturated aqueous NaCl-solution. The organic layer was then dried using MgSO4 and evaporated to yield 60 mg of the title compound that was used without further purification.
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted twice
- washThe combined organic layers were washed twice
- customThe organic layer was then dried
- customevaporated
Sources & evidence
- ORD record
- ord-f165596ad9d6464db46cb01823ea9978
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018383B2
Reaction notes
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