Methanesulfonyl chloride → Matairesinol Mesylate

HRID 490782Notes

Reaction equation

HRID 490782 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C@@H:11]2[C@@H:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([O:24][CH3:25])[CH:23]=3)[C:14](=[O:15])[O:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[OH:9].[S:27]([O-:2])(=[O:29])(=[O:28])[CH3:30]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 119205(-)-Matairesinol

Product 1

HCID 131727439Matairesinol Mesylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Matairesinol (500 mg, 1.4 mmol) was dissolved in 50 ml pyridine. To the solution stirred at room temperature, mesyl chloride (Methanesulfonyl chloride, 642 mg, 5.6 mmol) was added dropwise. The mixture was heated and stirred at 50° C. for 3 h. The solvent was then removed under reduced pressure and the residue extracted with dichloromethane (50 ml) and water (2×25 ml). The organic phase was dried over NaSO4 and the solvent removed. The residue was chromatographed on a silica column using CHCl3:EtOAc (1:1) as eluent. Yield 543 mg, 75.5%, slightly yellow-brown oil, purity>90% (NMR).

Workup

  1. temperatureThe mixture was heated
  2. stirringstirred at 50° C. for 3 h
  3. customThe solvent was then removed under reduced pressure
  4. extractionthe residue extracted with dichloromethane (50 ml) and water (2×25 ml)
  5. dry with materialThe organic phase was dried over NaSO4
  6. customthe solvent removed
  7. customThe residue was chromatographed on a silica column

Sources & evidence

ORD record
ord-97c5b4b0212640faabd1be6709594a1a
Source dataset
uspto-grants-2009_05
Patent number
US07528166B2

Reaction notes

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