Water → 3-Benzylsulfonyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid

HRID 1830150Notes

Reaction equation

HRID 1830150 reaction equation
[CH2:1]([S:8][CH2:9][CH:10]([CH2:14][O:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:22]OS([O-])=O.[K+].[OH2:28]>CO>[CH2:1]([S:8]([CH2:9][CH:10]([CH2:14][O:15][CH:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)[C:11]([OH:13])=[O:12])(=[O:22])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 220539503-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 220539743-Benzylsulfonyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid (1.16 g, 3.7 mmol) in a mixture of MeOH (10 ml) and water (30 ml) was treated oxone (3.5 g, 5.6 mmol) overnight. Methanol evaporated off under reduced pressure, aqueous layer extracted with ethyl acetate, dried (Na2SO4) and evaporated under reduced pressure to give the title compound as white solid (1.36 g); MS: 365 (M+Na), 343 (MH+); LCMS retention time 3.1 minutes.

Workup

  1. customMethanol evaporated off under reduced pressure, aqueous layer
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1b94bcd4e5f7488487ffaebaa4282f5a
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

Loading…