Methanesulfonic Acid → Methanesulfonic Acid

HRID 389847Notes

Reaction equation

HRID 389847 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].O.[CH3:7][S:8]([OH:11])(=[O:10])=[O:9]>C(O)(C)C>[S:2]([O-:5])(=[O:4])(=[O:3])[CH3:1].[CH3:7][S:8]([OH:11])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 57449004HCID 57449004, compound

Product 2

HCID 6395Methanesulfonic AcidHCID 85257Methanesulfonate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
45 °C

Procedure

To a 25-mL 3-neck flask under an inert nitrogen atmosphere, 3 mL of isopropanol (IPA) was charged. A slurry was prepared by adding 225 mg amorphous free base of Compound 1 to the flask. The slurry was warmed to a temperature of 45° C. Methanesulfonic acid hydrate (98.0 mg) was then added to the slurry. The slurry was stirred at 45° C. for one hour, then cooled to 22° C. to produce a thick crystalline slurry. The slurry was filtered and washed with IPA (2×1 mL). Excess IPA was removed from the crystalline cake by drying at 55° C. for more than two hours to achieve a constant weight. Crystalline mesylate (methanesulfonic acid) salt of Compound 1 (180 mg) was isolated. It was determined that the crystalline mesylate salt was unstable at 5° C.

Workup

  1. customA slurry was prepared
  2. temperaturecooled to 22° C.
  3. customto produce a thick crystalline slurry
  4. filtrationThe slurry was filtered
  5. washwashed with IPA (2×1 mL)
  6. customExcess IPA was removed from the crystalline cake
  7. customby drying at 55° C. for more than two hours

Sources & evidence

ORD record
ord-729dd9d746104b869c29095384e18008
Source dataset
uspto-grants-2013_02
Patent number
US08383610B2

Reaction notes

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