p-Toluenesulfonic acid → HCID 57659581, compound

HRID 1172586Notes

Reaction equation

HRID 1172586 reaction equation
[CH2:1]([N:8]1[C:12]([CH:13]2C(=O)O[C:16](C)(C)[O:15][C:14]2=[O:22])=[CH:11][C:10]([CH3:23])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>>[CH3:16][O:15][C:14](=[O:22])[CH2:13][C:12]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[C:10]([CH3:23])[CH:11]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57659598HCID 57659598, compound

Product 1

HCID 57659581HCID 57659581, compoundYield 96%

Conditions

Temperature
0 °C

Procedure

To the solution of 5-(2-benzyl-5-methyl-2H-pyrazol-3-yl)-2,2-dimethyl-[1,3]dioxane-4,6-dione obtained in step 1, pTsOH (3.74 g, 19.4 mmol) was added and stirring was continued for 2 h at 60° C. The reaction mixture was cooled to 0° C. and TEA (1.96 g, 19.4 mmol) was added drop by drop. Stirring was continued for 15 minutes. The mixture was concentrated under reduced pressure, the residue taken up into DCM (30 ml), washed with water (2×15 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 1.03 g (96%) of (2-benzyl-5-methyl-2H-pyrazol-3-yl)-acetic acid methyl ester which was used in the next step without further purification. LC-MS: tR=0.83 min; [M+H]+=245.16.

Workup

  1. stirringStirring
  2. waitwas continued for 15 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washwashed with water (2×15 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c04abb84ecc40d2a4ebc5a80c594bfe
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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