p-Toluenesulfonic acid → HCID 67385068, compound

HRID 1471939Notes

Reaction equation

HRID 1471939 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][CH2:13][C@@H:14]([OH:17])[CH2:15][OH:16])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:20](OC)([CH3:22])[CH3:21].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:21][C:20]1([CH3:22])[O:17][C@H:14]([CH2:13][CH2:12][C:10]2[NH:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[CH2:15][O:16]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 67384826HCID 67384826, compound

Product 1

HCID 67385068HCID 67385068, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-4-(3-phenyl-1H-pyrazol-5-yl)butane-1,2-diol (2.5 g, 10.76 mmol) in acetone (50 mL), were added 2,2-dimethoxypropane (11.21 g, 108 mmol) and PTSA (0.185 g, 1.076 mmol) at room temperature. After stirring for 3 h, the reaction was concentrated under reduced pressure. The resulting residue was poured into water and extracted with ethyl acetate. The extract was dried over MgSO4 and concentrated under reduced pressure to give the title compound without further purification. LCMS m/z=273.4 [M+H]+.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additionThe resulting residue was poured into water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50cb89c0714049feb85e06065156f25d
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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