Adipic Acid → HCID 25056529, compound

HRID 1660773Notes

Reaction equation

HRID 1660773 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:38])(=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35]>C(OCC)(=O)C.CC(C)=O.O>[C:29]([OH:38])(=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35].[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 196Adipic AcidHCID 25022354Evogliptin

Product 1

HCID 25056529HCID 25056529, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

503 mg of the compound obtained in Example 11 was dissolved in 4 mL of ethyl acetate to which a solution of 183 mg of adipic acid in 3 mL of acetone/water (30/1(v/v)) 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 resulting mixture was stirred for 10 min and filtered to afford 336 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. customresulting mixture
  7. stirringwas stirred for 10 min
  8. filtrationfiltered

Sources & evidence

ORD record
ord-f7bc3ec53e3e46779c827723fae8a304
Source dataset
uspto-grants-2011_10
Patent number
US08030315B2

Reaction notes

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