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

HRID 1247835Notes

Reaction equation

HRID 1247835 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)-1H-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 citric acid. The resulting precipitate was collected by filtration and dried under reduced pressure to give 3-{[1-methyl-5-(tritylamino)-1H-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-ffab0411ba724787a87113080e15eacf
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

Loading…