L-Malic Acid → HCID 25056527, compound

HRID 1660771Notes

Reaction equation

HRID 1660771 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:37])(=[O:36])[C@H:30]([CH2:32][C:33]([OH:35])=[O:34])[OH:31]>CC(C)=O>[C:29]([OH:37])(=[O:36])[CH:30]([CH2:32][C:33]([OH:35])=[O:34])[OH:31].[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

4

Reactant 2

HCID 222656L-Malic AcidHCID 25022354Evogliptin

Product 1

HCID 25056527HCID 25056527, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

498 mg of the compound obtained in Example 11 was dissolved in 4 mL of acetone to which a solution of 166 mg of L-malic acid in 1 mL of acetone 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, and the resulting mixture was stirred for 10 min and filtered to afford 506 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. stirringthe resulting mixture was stirred for 10 min
  7. filtrationfiltered

Sources & evidence

ORD record
ord-1a3c583e314e4613a8dc325699fb513e
Source dataset
uspto-grants-2011_10
Patent number
US08030315B2

Reaction notes

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