Sodium Hydroxide → 3-{[1-Methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acid

HRID 459615Notes

Reaction equation

HRID 459615 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][C:28](=[O:35])[CH2:29][C:30]([O:32]CC)=[O:31])[CH:4]=[N:3]1.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([NH:27][C:28](=[O:35])[CH2:29][C:30]([OH:32])=[O:31])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21904531ethyl 3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoate

Product 1

HCID 219045813-{[1-Methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoate (1.3 g) in tetrahydrofuran (30 ml) was added 1N aqueous sodium hydroxide solution (3.1 ml) and the mixture was stirred at room temperature for 3 hours. Tetrahydrofuran was removed in vacuo and the residue was made acidic with diluted aqueous citric acid solution. The resulting precipitate was collected by filtration and dried under reduced pressure to give 3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acid (1.22 g).

Workup

  1. customTetrahydrofuran was removed in vacuo
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-c7bfbbbce15547bca3794f480616df20
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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