5-[2-((S)-2-Benzyloxycarbonyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester → 5-[2-((S)-2-carboxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1970454Notes

Reaction equation

HRID 1970454 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[C:20]([O:22]CC2C=CC=CC=2)=[O:21])=[O:14])[N:8]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[C:20]([OH:22])=[O:21])=[O:14])[N:8]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 668549795-[2-((S)-2-Benzyloxycarbonyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 668544075-[2-((S)-2-carboxy-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 13.2 g 5-[2-((S)-2-benzyloxycarbonyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-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 (3 bar) for 6 h. The reaction mixture was filtered over a plug of Celite and washed with ethanol giving the crude product after evaporation of the solvents which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over a plug of Celite
  2. washwashed with ethanol giving the crude product
  3. customafter evaporation of the solvents which
  4. customwas used without further purification

Sources & evidence

ORD record
ord-7c035e1425d04a5091789180ba4c4a23
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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