Oxalic Acid → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amide oxalate

HRID 719679Notes

Reaction equation

HRID 719679 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][S:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:8].[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].CCOCC>CC(C)=O>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[CH3:32][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][S:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 103471824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amide

Product 1

HCID 103471814'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amide oxalateYield 38.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Dissolved 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amide (0.48 g, 1.07 mmol, 1 eq.) in acetone (10 mL) and treated the solution dropwise with oxalic acid(0.12 g, 1.28 mmol, 1.2 eq.) in acetone (5 mL). Added Et2O until cloudy and then placed in the freezer to induce crystallization. The resulting white solid was collected by filtration and washed with Et2O to give 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amide oxalate (0.2217 g).

Workup

  1. customcrystallization
  2. filtrationThe resulting white solid was collected by filtration
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-a3b96aeb213a43cc9e01ca5a60ccbd40
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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