Methanesulfonic Acid → 934240-35-4

HRID 1691498Notes

Reaction equation

HRID 1691498 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 (E1, 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-bbaa47ca17a34d1bb739b957d53f8330
Source dataset
uspto-grants-2012_04
Patent number
US08153681B2

Reaction notes

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