Sodium Hydroxide → 4-[4-(2-Adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid
Reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)[C:18]=1[S:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH2:8]2.[OH-].[Na+]>CO>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[C:18]=1[S:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH2:8]2Participants
4
Procedure
Methyl 4-[4-(2-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (190 mg, 0.42 mmol) (Intermediate #2) was dissolved in methanol (10 mL) and treated at ambient temperature with 2M aqueous sodium hydroxide solution (1.05 mL, 2.1 mmol). The mixture was stirred at ambient temperature for 18 h. and then heated to 65° C. for a further 2 h. Methanol was removed by evaporation under reduced pressure and the clear solution diluted with water (25 ml). 2M HCl was added to pH4 and the mixture extracted with ethyl acetate (2×25 mL). The combined extracts were washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated to give the title compound as a white solid. (174 mg, 94%)
Workup
- temperatureheated to 65° C. for a further 2 h
- customMethanol was removed by evaporation under reduced pressure
- additionthe clear solution diluted with water (25 ml)
- addition2M HCl was added to pH4
- extractionthe mixture extracted with ethyl acetate (2×25 mL)
- washThe combined extracts were washed with water (2×10 mL) and brine (10 mL)
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-1009b57a74254286ad033bcf1f6aeb83
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344016B2
Reaction notes
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