p-Toluenesulfonic acid → HCID 71239369, compound

HRID 2171603Notes

Reaction equation

HRID 2171603 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20]C3CCCCO3)[C@@H:13]3[C@H:18]([OH:19])[CH2:17][CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([OH:20])[C@@H:13]3[C@H:18]([OH:19])[CH2:17][CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 71239171HCID 71239171, compound

Product 1

HCID 71239369HCID 71239369, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-chloro-4-((3S,3aS,4R)-4-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile (30 mg, 0.088 mmol) in methanol (1 mL) was added p-toluenesulfonic acid (20 mg, 0.1058 mmol) and the reaction mixture was stirred at room temperature for overnight. Methanol was evaporated from reaction mixture and extracted with EtOAc. Organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography over silica gel using 3% MeOH in DCM provided the title compound.

Workup

  1. customMethanol was evaporated from reaction mixture
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography over silica gel using 3% MeOH in DCM

Sources & evidence

ORD record
ord-b1394596cc5c475191b629e825ca3455
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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