Methanesulfonic Acid → 934240-35-4

HRID 2264847Notes

Reaction equation

HRID 2264847 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[NH:20][C@H:19]([C:21]([NH2:23])=[O:22])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[CH3:24][S:25]([OH:28])(=[O:27])=[O:26]>CCOC(C)=O>[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[NH:20][C@H:19]([C:21]([NH2:23])=[O:22])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 16046068Raxatrigine

Product 1

HCID 86624720934240-35-4

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

EtOAc (6 ml) was added to (5R)-5-(4-{[(2-Fluorophenyl)methyl]oxy}phenyl)-L-prolinamide (E4, 300 mg) and this was heated at 60° C. for an hour to dissolve the compound. Then methanesulfonic acid (65 μl, 1.05 eq) was added to the solution and as soon as the acid was added, the solution went cloudy. This was then left to temperature cycle (0-40° C.) for 2 days. The compound was isolated by filtration as a white solid, washed with EtOAc and dried in vacuo at 40° C. overweek-end to afford 335 mg of the title compound.

Workup

  1. dissolutionto dissolve the compound
  2. additionas soon as the acid was added
  3. customThe compound was isolated by filtration as a white solid
  4. washwashed with EtOAc
  5. customdried in vacuo at 40° C. overweek-end

Sources & evidence

ORD record
ord-6c9a1843a1864aed8d7e9e96f2895667
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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