Methanol → (4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid
Reaction equation
C([O:3][C:4](=[O:25])[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:22]2[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)[O:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)C.[OH-].[Li+].C1COCC1.CO>O>[CH:22]1([S:19]([C:16]2[CH:15]=[CH:14][C:13]([CH:5]([O:6][CH:7]3[CH2:8][CH2:9][O:10][CH2:11][CH2:12]3)[C:4]([OH:25])=[O:3])=[CH:18][CH:17]=2)(=[O:21])=[O:20])[CH2:24][CH2:23]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To (4-cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid ethyl ester (23.2 gm, 62.87 mmol) was added a solution of lithium hydroxide (13.0 gm, 314.36 mmol) in water (150 ml) followed by THF (200 ml) and methanol (10 ml) and stirred for 2 hours at 25° C. Organic solvents were evaporated from the reaction mixture and aqueous layer was acidified 1N HCl, extracted with ethyl acetate (3×200 ml), organic layer was washed with brine solution, dried over anhydrous sodium sulfate, and washed concentrated under reduced pressure to provide (4-cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid (18.49 gm)
Workup
- customOrganic solvents were evaporated from the reaction mixture and aqueous layer
- extractionextracted with ethyl acetate (3×200 ml), organic layer
- washwas washed with brine solution
- dry with materialdried over anhydrous sodium sulfate
- washwashed
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f7ebd74fdab041e3b814f3e33d0cc9a9
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501955B2
Reaction notes
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