Ethanol → 5-[(2,4-Dimethylphenyl)(2-methylpropyl)sulfamoyl]-2-(oxan-4-ylmethoxy)benzoic acid
Reaction equation
C([C:3]1[CH:4]=[C:5]([S:17]([N:20]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[CH3:32])[CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:19])=[O:18])[CH:6]=C[C:8]=1[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)#N.[OH-:33].[Na+].[CH2:35]([OH:37])[CH3:36]>>[CH3:32][C:26]1[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:25]=1[N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:17]([C:5]1[CH:4]=[CH:3][C:8]([O:9][CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:36]([CH:6]=1)[C:35]([OH:33])=[O:37])(=[O:19])=[O:18]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 3-cyano-N-(2,4-dimethylphenyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (50 mg, 0.110 mmol) in ethanol (1 mL) at 25° C. was added sodium hydroxide (0.548 mL, 2.190 mmol). After which the reaction mixture was stirred at 80° C. for 15 hours, then cooled, ethanol removed and crude partitioned between ethyl acetate (20 mL) and HCl (2N, 15 mL). The organic layer was separated, dried over MgSO4 and the solvent removed in vacuo to give a yellow oil. The crude was purified by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were evaporated in vacuo to give the required product, 16.1 mg. LCMS [LCMS2] Rt 0.91 mins, m/z (ES+) 476 (M+H).
Workup
- temperaturecooled
- customethanol removed
- customcrude partitioned between ethyl acetate (20 mL) and HCl (2N, 15 mL)
- customThe organic layer was separated
- dry with materialdried over MgSO4
- customthe solvent removed in vacuo
- customto give a yellow oil
- customThe crude was purified by mass
- customThe relevant fractions were evaporated in vacuo
Sources & evidence
- ORD record
- ord-b8beaf17d190435ab3545edc81145c93
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428452B2
Reaction notes
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