Citric Acid → HCID 66990073, compound

HRID 454741Notes

Reaction equation

HRID 454741 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]([CH2:42][CH3:43])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[C:19]([NH:27][C:28]([C:30]2[CH:31]=[N:32][CH:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:35]=2)=[O:29])[CH:18]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(Cl)(Cl)Cl>CO.O1CCOCC1>[C:3]([O:7][C:8]([N:10]([CH2:42][CH3:43])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[C:19]([NH:27][C:28]([C:30]2[CH:31]=[N:32][CH:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:35]=2)=[O:29])[CH:18]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 66990363HCID 66990363, compound

Product 1

HCID 66990073HCID 66990073, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (3.8 mL) was added to a solution mixture of methyl 4-(2-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate (0.84 g) in methanol (4.2 mL) and dioxane (4.2 mL) at room temperature, followed by stirring at the same temperature for 3 hours and 10 minutes. After adjusting the pH to 4.9 with a 10% aqueous solution of citric acid, chloroform was added thereto. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.80 g of 4-(2-((tert-butoxycarbonyl)(ethyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a white solid.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-bffd67905afa4aa7a4e3af4efbe39f8f
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

Loading…