Citric Acid → HCID 25056267, compound

HRID 1660768Notes

Reaction equation

HRID 1660768 reaction equation
[NH2:1][C@H:2]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C@H:7]1[CH2:13][O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:5].[C:29]([OH:41])(=[O:40])[CH2:30][C:31]([CH2:36][C:37]([OH:39])=[O:38])([C:33]([OH:35])=[O:34])[OH:32]>C(O)C.O>[C:29]([OH:41])(=[O:40])[CH2:30][C:31]([CH2:36][C:37]([OH:39])=[O:38])([C:33]([OH:35])=[O:34])[OH:32].[NH2:1][C@H:2]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[C@H:7]1[CH2:13][O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:5]

Participants

5

Reactant 2

HCID 311Citric AcidHCID 25022354Evogliptin

Product 1

HCID 25056267HCID 25056267, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

496 mg of the compound obtained in Example 11 was dissolved in 2 mL of ethanol, to which a solution of 273 mg of anhydrous citric acid in 1 mL of water was then slowly added, followed by stirring for 30 min. The reaction mixture was concentrated, to which 2 mL of ethyl acetate and 1 mL of 2-propanol were then added followed by stirring. 15 mL of hexane was added thereto followed by stirring for 10 min and filtration to afford 637 mg of the title compound as a solid.

Workup

  1. additionwas then slowly added
  2. concentrationThe reaction mixture was concentrated, to which 2 mL of ethyl acetate and 1 mL of 2-propanol
  3. additionwere then added
  4. stirringby stirring
  5. addition15 mL of hexane was added
  6. stirringby stirring for 10 min
  7. filtrationfiltration

Sources & evidence

ORD record
ord-bc17f253fb41498dab6141d6ccaf4dbc
Source dataset
uspto-grants-2011_10
Patent number
US08030315B2

Reaction notes

Loading…