methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate → 4-(4(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acid
Reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=[C:10]([CH2:25][N:26]([CH3:31])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.O.ClCCl.Cl>[C:1]([O:5][C:6](=[O:32])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[C:10]([CH2:25][N:26]([CH3:31])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:9]=1)([CH3:3])([CH3:2])[CH3:4]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Procedure
To a stirred solution of methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-((N -methylmethylsulfonamido)methyl)phenoxy)benzoate (370 mg, 0.797 mmol) in dioxane (8 ml) was added a solution of LiOH monohydrate (43.5 mg, 1.04 mmol) in water (2 ml) (0.1 M solution 4:1 dioxane/water). The reaction was stirred for 5 hours, then diluted with dichloromethane and 2 N HCl. The aqueous phase was extracted with dichloromethane and the combined organic layers were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography to give 4-(4-(2-tert-butoxy-2-oxoethyl)-2-((N -methylmethylsulfonamido)methyl)phenoxy)benzoic acid (0.253 g).
Workup
- extractionThe aqueous phase was extracted with dichloromethane
- washthe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- customThe crude product was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-8a9d0246067643f5b4d9f007217a43c2
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183289B2
Reaction notes
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