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

HRID 628772Notes

Reaction equation

HRID 628772 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]; 1H-NMR (500 MHz, CHLOROFORM-d) δ ppm 1.71 (6 H, s), 1.94-2.12 (4 H, m), 3.47 (2 H, td, J=11.41, 2.98 Hz), 3.73-3.86 (1 H, m), 4.07-4.15 (2 H, m), 6.82 (1 H, br. s.)

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-44f21f7672da4d20a39a76af5d7dfead
Source dataset
uspto-grants-2016_04
Patent number
US09315454B2

Reaction notes

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