Citric Acid → HCID 66990757, compound

HRID 454579Notes

Reaction equation

HRID 454579 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:43]=[CH:42][C:41]([C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[CH:40][C:8]=1[C:9]([NH:11][C:12]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:31](C(OC(C)(C)C)=O)[CH3:32])[CH:22]=[CH:21][C:13]=1[C:14]([O:16]C(C)(C)C)=[O:15])=[O:10])(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(Cl)(Cl)[Cl:64]>CO.O1CCOCC1>[ClH:64].[ClH:64].[OH:6][C:7]1[CH:43]=[CH:42][C:41]([C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[CH:40][C:8]=1[C:9]([NH:11][C:12]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][CH3:32])[CH:22]=[CH:21][C:13]=1[C:14]([OH:16])=[O:15])=[O:10]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 66990244HCID 66990244, compound

Product 1

HCID 66990757HCID 66990757, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (2.3 mL) was added to a solution mixture of tert-butyl 2-(2-acetoxy-5-(pyridin-3-yl)benzamido)-4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)benzoate (0.28 g) in methanol (2 mL) and dioxane (4 mL), followed by stirring at room temperature for 6 hours. The reaction mixture was adjusted to a pH of 5.5 with a 10% aqueous solution of citric acid, and chloroform was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Trifluoroacetic acid (4 mL) was added to the obtained residue, followed by stirring at room temperature for 20 minutes. The solvent was evaporated under reduced pressure, and toluene was added to the residue. The solvent was evaporated under reduced pressure, and a 4 mol/L hydrogen chloride-dioxane solution (5 mL) was added to the residue, followed by stirring at room temperature for 5 minutes. The solvent was evaporated under reduced pressure, and diethyl ether was added to the residue. The solid substance was collected by filtration to obtain 0.18 g of 2-(2-hydroxy-5-(pyridin-3-yl)benzamido)-4-(2-(methylamino)phenyl)benzoic acid dihydrochloride as a light yellow solid.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionTrifluoroacetic acid (4 mL) was added to the obtained residue
  7. stirringby stirring at room temperature for 20 minutes
  8. customThe solvent was evaporated under reduced pressure, and toluene
  9. additionwas added to the residue
  10. customThe solvent was evaporated under reduced pressure
  11. additiona 4 mol/L hydrogen chloride-dioxane solution (5 mL) was added to the residue
  12. stirringby stirring at room temperature for 5 minutes
  13. customThe solvent was evaporated under reduced pressure, and diethyl ether
  14. additionwas added to the residue
  15. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-9346f99ea8204e3a97390025d9502846
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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