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

HRID 538628Notes

Reaction equation

HRID 538628 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 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 RT for 2.5 d. The organic solvent is removed under reduced pressure and the aq. residue is diluted with water (2 L) and washed with DCM (2 L). The aq. layer is acidified to pH 1-2 with concentrated HCl and then extracted with DCM (3×2 L). The acidic aqueous layer 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. Yield: 83%; ESI-MS: 235 [M+H]+

Workup

  1. customThe organic solvent is removed under reduced pressure
  2. additionthe aq. 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-8ccedbacda9d41f6b33bcab43b3a1f4e
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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