Sodium Hydroxide → 2-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid
Reaction equation
C([O:3][C:4](=[O:18])[C:5]([CH3:17])([S:7]([CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)(=[O:9])=[O:8])[CH3:6])C.[OH-].[Na+].CC(OC)(C)C>C1COCC1>[CH3:17][C:5]([S:7]([CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)(=[O:9])=[O:8])([CH3:6])[C:4]([OH:18])=[O:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 123 g (0.44 mol) of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid ethyl ester in THF (450 mL) are added 663 mL of 2M aqueous sodium hydroxide solution (1.33 mol). The reaction is stirred at room temperature for 1 h. To the reaction mixture is added TBME (1.25 L) and the layers are separated. The aqueous layer is cooled in an ice bath and then acidified with 37% aqueous HCl solution (123 mL). The resulting precipitate is isolated by filtration, washed with water (200 mL) and dried under reduced pressure at 50° C. to afford 101 g of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid as white crystalline solids. Yield: 91%; ES-MS: m/z 251 [M+H]; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31-1.45 (2H, m), 1.49 (6H, s), 1.70-1.79 (2H, m), 2.13-2.28 (1H, m), 3.24 (2H, d, J=6.60 Hz), 3.28-3.38 (2H, m), 3.76-3.85 (2H, m), 13.65 (1H, br. s.)
Workup
- customthe layers are separated
- temperatureThe aqueous layer is cooled in an ice bath
- customThe resulting precipitate is isolated by filtration
- washwashed with water (200 mL)
- customdried under reduced pressure at 50° C.
Sources & evidence
- ORD record
- ord-ea4198df1fcc4c498709d75c07bfc3f8
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362039B2
Reaction notes
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