Oxalic Acid → 4-[(S)-2-Aminopropionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide dioxalate

HRID 2523

Reaction equation

HRID 2523 reaction equation
[NH2:1][C@@H:2]([CH3:41])[C:3]([NH:5][CH2:6][C:7]1[CH:40]=[CH:39][C:10]([C:11]([N:13]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([C:30](=[O:38])[C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:26][CH2:25]2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[O:12])=[CH:9][CH:8]=1)=[O:4].[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44]>CO>[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44].[C:42]([OH:47])(=[O:46])[C:43]([OH:45])=[O:44].[NH2:1][C@@H:2]([CH3:41])[C:3]([NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([N:13]([CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([C:30](=[O:38])[C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[CH2:28][CH2:29]2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[O:12])=[CH:39][CH:40]=1)=[O:4]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 678007174-[(S)-2-Aminopropionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide

Product 1

HCID 867522934-[(S)-2-Aminopropionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide dioxalateYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[(S)-2-Aminopropionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (84.7 mg, 0.155 mmol) was dissolved in methanol (5 ml) and mixed with oxalic acid (28 mg, 0.311 mmol). After 5 minutes of stirring at room temperature, methanol was removed by evaporation, and the resulting amorphous residue was washed with acetone (5 ml) and collected by filtration to obtain 84 mg (85.1%) of the title compound in a colorless amorphous powder form.

Workup

  1. custommethanol was removed by evaporation
  2. washthe resulting amorphous residue was washed with acetone (5 ml)
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6520b67c10374e1083985864bd8780e4
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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