(R)-benzyl 1-(2-(2-(tert-butoxycarbonylamino)acetoxy)propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate → (R)-1-(2-(2-(tert-butoxycarbonylamino)acetoxy)propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid

HRID 1517845Notes

Reaction equation

HRID 1517845 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12][C@H:13]([CH3:38])[CH2:14][N:15]1[C:19]([CH3:20])=[C:18]([C:21]([O:23]CC2C=CC=CC=2)=[O:22])[C:17](=[O:31])[N:16]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12][C@H:13]([CH3:38])[CH2:14][N:15]1[C:19]([CH3:20])=[C:18]([C:21]([OH:23])=[O:22])[C:17](=[O:31])[N:16]1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86645603(R)-benzyl 1-(2-(2-(tert-butoxycarbonylamino)acetoxy)propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate

Product 1

HCID 66670730(R)-1-(2-(2-(tert-butoxycarbonylamino)acetoxy)propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acidYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-benzyl 1-(2-(2-(tert-butoxycarbonylamino)acetoxy)propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate (485 mg, 0.926 mmol) and 10% Pd/C (60 mg) in methanol (8 mL) was stirred for 3 h at rt. TLC analysis showed that the starting material was consumed completely. The catalyst was removed by filtration and the reaction mixture was concentrated in vacuo. The residue was purified by a silica gel column chromatography (100% EtOAc) to afford the title compound as a yellow solid (172 mg, 43% yield).

Workup

  1. customwas consumed completely
  2. customThe catalyst was removed by filtration
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-662fe006018446ee82a36afc311c9ac7
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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