Lithium Hydroxide → 3-[(2-tert-Butoxy-2-oxo-1-phenyl-ethyl)sulfamoyl]benzoic acid
Reaction equation
[C:1]([O:5][C:6](=[O:28])[CH:7]([NH:14][S:15]([C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23]C)=[O:22])(=[O:17])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.CO>[C:1]([O:5][C:6](=[O:28])[CH:7]([NH:14][S:15]([C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([OH:23])=[O:22])(=[O:17])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To a stirring solution of methyl 3-[(2-tert-butoxy-2-oxo-1-phenylethyl)-sulfamoyl]benzoate (2.2 g, 5.4 mmol) in tetrahydrofuran (33.7 mL) and methanol (33.7 mL) was added 1.0 N aqueous lithium hydroxide (13.5 mL, 13.5 mmol) in one portion. The reaction mixture was stirred for 18 hours at ambient temperature, after which time the mixture was concentrated under reduced pressure. The resulting crude was partitioned between ethyl acetate (20 mL) and water (40 mL); the resulting aqueous was acidified with concentrated sulphuric acid (c. 1.0 mL) and washed with ethyl acetate (2×20 mL). The organic phases were combined, dried over magnesium sulfate and concentrated under reduced pressure to yield the title compound as a white solid (1.21 g, 57%).
Workup
- concentrationafter which time the mixture was concentrated under reduced pressure
- customThe resulting crude was partitioned between ethyl acetate (20 mL) and water (40 mL)
- washwashed with ethyl acetate (2×20 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-02b2a924a25c46cca20c6ae2274ef77b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090606B2
Reaction notes
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