5-Benzyloxycarbonylmethoxy-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester → 5-Carboxymethoxy-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1970452Notes

Reaction equation

HRID 1970452 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])[N:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:7]=1)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([OH:15])=[O:14])[N:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 668548175-Benzyloxycarbonylmethoxy-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 668550565-Carboxymethoxy-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 15.5 g 5-benzyloxycarbonylmethoxy-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester in 100 ml ethyl acetate was added 1 g Pd/C (10%) and the resulting suspension stirred under an atmosphere of hydrogen (1 bar) for 24 h. The reaction mixture was filtered over a plug of Celite, washed with ethyl acetate and methanol giving the crude product after evaporation of the solvents. Yield: 9.5 g colorless platelets.

Workup

  1. filtrationThe reaction mixture was filtered over a plug of Celite
  2. washwashed with ethyl acetate and methanol giving the crude product
  3. customafter evaporation of the solvents

Sources & evidence

ORD record
ord-65fd3fbdc3bb4a2e9872d85f686d818a
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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