p-Toluenesulfonic acid monohydrate → HCID 86650871, compound

HRID 1967568Notes

Reaction equation

HRID 1967568 reaction equation
[CH3:1][C:2]([NH:14][C@@H:15]1[CH2:19][C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[CH:21]=2)[N:17]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[C:16]1=[O:41])([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[N:5]=1)[CH3:3].O.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1>C(O)(C)C>[S:49]([C:46]1[CH:47]=[CH:48][C:43]([CH3:53])=[CH:44][CH:45]=1)([OH:52])(=[O:51])=[O:50].[CH3:3][C:2]([NH:14][C@@H:15]1[CH2:19][C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:28])([F:29])[F:30])[CH:21]=2)[N:17]([C:31]2[CH:32]=[CH:33][C:34]([C:37]([F:38])([F:40])[F:39])=[CH:35][CH:36]=2)[C:16]1=[O:41])([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([F:11])([F:13])[F:12])[N:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 44247760HCID 44247760, compound

Product 1

HCID 86650871HCID 86650871, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Dissolve (3R,5R)-3-[1-methyl-1-(2-trifluoromethyl-pyrimidin-4-yl)-ethylamino]-5-(3-trifluoromethoxy-phenyl)-1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one (4.57 g, 7.71 mmol) in isopropanol (10 mL). Add p-toluenesulfonic acid monohydrate (1.49 g, 7.71 mmol) and heat to 45° C. until the solution is homogeneous. Cool to ambient temperature and add seed crystals. Let stand at ambient temperature for 64 hours. Filter the precipitate and wash with heptane. Dry under vacuum for 4 hours to give (3R,5R)-3-[1-methyl-1-(2-trifluoromethyl-pyrimidin-4-yl)-ethylamino]-5-(3-trifluoromethoxy-phenyl)-1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one tosylate (5.06 g, 86%) as a white powder. LC-MS ESI m/z: 593 (M+H)+, Tr=4.92 min., method 1.

Workup

  1. additionadd seed crystals
  2. filtrationFilter the precipitate
  3. washwash with heptane
  4. customDry under vacuum for 4 hours

Sources & evidence

ORD record
ord-e73ceaa8a9204463acaead880a7c8b03
Source dataset
uspto-grants-2013_04
Patent number
US08420654B2

Reaction notes

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