Sodium Hydroxide → 2-Methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acid

HRID 553596Notes

Reaction equation

HRID 553596 reaction equation
C([O:3][C:4](=[O:17])[C:5]([CH3:16])([S:7]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)(=[O:9])=[O:8])[CH3:6])C.[OH-].[Na+]>O1CCOCC1.O>[CH3:16][C:5]([S:7]([CH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)(=[O:8])=[O:9])([CH3:6])[C:4]([OH:17])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 597039772-Methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acid ethyl ester

Product 1

HCID 597040272-Methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acidYield 83%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 166 g (0.63 mol) of 2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acid ethyl ester in THF/water (4/1, 1.66 L) are added 50.5 g (1.26 mol) of NaOH pellets in portions over 20 min. The reaction is stirred at room temperature for 2.5 d. The organic solvent is removed under reduced pressure and the aqueous residue is diluted with water (2 L) and washed with DCM (2 L). The aqueous layer is acidified to pH 1-2 with concentrated HCl and then extracted with DCM (3×2 L). The acidic aqueous is further saturated with NaCl and extracted again with DCM (6×2 L). The combined organic extracts are concentrated under reduced pressure to give 123 g of 2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acid as a white solid. Yield: 83%, ES-MS: m/z 235 [M−H]

Workup

  1. customThe organic solvent is removed under reduced pressure
  2. additionthe aqueous residue is diluted with water (2 L)
  3. washwashed with DCM (2 L)
  4. extractionextracted with DCM (3×2 L)
  5. extractionextracted again with DCM (6×2 L)
  6. concentrationThe combined organic extracts are concentrated under reduced pressure

Sources & evidence

ORD record
ord-668b418bc2114957b69ef683db2c97af
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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