Methanesulfonic Acid → HCID 69283383, compound

HRID 2252367Notes

Reaction equation

HRID 2252367 reaction equation
[Na+].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@@H:10]([O:14][CH3:15])[C:11]([O-:13])=[O:12])=[CH:5][CH:4]=1.[CH3:16]S(O)(=O)=O>CO>[CH3:16][O:12][C:11](=[O:13])[C@H:10]([O:14][CH3:15])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 69285315HCID 69285315, compound

Product 1

HCID 69283383HCID 69283383, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (a), (R)-3-(4-hydroxy-phenyl)-2-methoxy-propionic acid sodium salt, (Example 2, Step 5) (5.00 g, 22.9 mmol) is dissolved in methanol (125 mL) and treated with methanesulfonic acid (7.44 mL, 114.6 mmol). The reaction is stirred at room temperature for 1 h. The reaction is concentrated in vacuo and the resulting residue taken up in diethyl ether. The organic portion is washed with water (2×) and saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated in vacuo to yield 4.00 g (83%) of an off-white solid. The material is used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.06 (dd, J=2.2, 6.4 Hz, 2H), 6.72 (dd, J=2.2, 6.4 Hz, 2H), 5.38 (bd s, 1H), 3.95 (dd, J=5.3, 7.1 Hz, 1H), 3.71 (s, 3H), 3.35 (s, 3H), 2.95 (m, 2H); MS (electrospray), 209.2 (ES−).

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. washThe organic portion is washed with water (2×) and saturated NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a99201460809404181dffc29c038e258
Source dataset
uspto-grants-2008_01
Patent number
US07321056B2

Reaction notes

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