Lithium Hydroxide → HCID 67482128, compound
Reaction equation
C[O:2][C:3](=[O:23])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([Cl:22])[CH:13]=1)[CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][S:8][CH2:7]1.[OH-].[Li+]>CO>[Cl:22][C:14]1[CH:13]=[C:12]([CH:4]([CH2:5][C@H:6]2[CH2:11][CH2:10][CH2:9][S:8][CH2:7]2)[C:3]([OH:23])=[O:2])[CH:17]=[CH:16][C:15]=1[S:18]([CH3:21])(=[O:20])=[O:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3(R)-(tetrahydro-thiopyran-3-yl)-propionic acid methyl ester (247 mg, 0.655 mmol) in methanol (4.75 mL) was treated with a 0.8M aqueous lithium hydroxide solution (7.27 mL, 5.895 mmol). The reaction mixture was stirred at 25° C. for 1.5 h and then concentrated in vacuo to remove methanol. The remaining aqueous layer was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford pure 2-(3-chloro-4-methanesulfonyl-phenyl)-3(R)-(tetrahydro-thiopyran-3-yl)-propionic acid (227.0 mg, 95.5%) as a light yellow foam: [α]23589=+12.21° (c=0.79, methanol).
Workup
- concentrationconcentrated in vacuo
- customto remove methanol
- extractionextracted with ethyl acetate (2×100 mL)
- washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ca39dc7f3bbf47a0bcee0da6aefe1617
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105671B2
Reaction notes
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