p-Toluenesulfonic acid → HCID 71241133, compound

HRID 2171606Notes

Reaction equation

HRID 2171606 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([Cl:35])[C:28]=3[CH3:36])[C@H:15]2[O:17][CH2:18][CH2:19][O:20]C2CCCCO2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Si:1]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[C:29]([Cl:35])[C:28]=3[CH3:36])[C@H:15]2[O:17][CH2:18][CH2:19][OH:20])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 131732946HCID 131732946, compound

Product 1

HCID 71241133HCID 71241133, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 4-((3S,3aR,4S)-4-((tert-butyldimethylsilyl)oxy)-3-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile (160 mg, 0.299 mmol) in methanol (5 mL) at room temperature was added p-toluenesulphonic acid and stirred for 1 h. Once the starting material had disappeared (monitored by TLC) methanol was removed from the reaction mixture and then extracted with EtOAc. Organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Crude product was purified by column chromatography using 15% in ethylacetate in hexane as solvent.

Workup

  1. customwas removed from the reaction mixture
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customCrude product was purified by column chromatography

Sources & evidence

ORD record
ord-3dde8cbe9bdc472a969de3d2c883ebf4
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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