Methanesulfonyl chloride → HCID 57429671, compound

HRID 889049Notes

Reaction equation

HRID 889049 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH2:8]2)=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[O:11][N:10]=[C:9]([CH2:12][O:13][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:8]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 57429670HCID 57429670, compound

Product 1

HCID 57429671HCID 57429671, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of solution of [5-(4-Fluoro-benzyl)-4,5-dihydro-isoxazol-3-yl]-methanol (80 mg, 0.38 mmol), TEA (57 mg, 0.57 mmol) in DCM (10 ml), methanesulfonyl chloride (43 mg, 0.38 mmol) was added slowly at 0° C. and the mixture was stirred at room temperature for 3 hrs. Aqueous NaHCO3 was added to the reaction mixture and extracted with methylene dichloride. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue obtained was purified by column chromatography to obtain Methanesulfonic acid 5-(4-fluoro-benzyl)-4,5-dihydro-isoxazol-3-ylmethyl ester (82 mg, 75%) as brown oil.

Workup

  1. additionwas added slowly at 0° C.
  2. extractionextracted with methylene dichloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f0d58c1cceec462dafc54e176a6b04ce
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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