Ethyl Acetate → Evogliptin

HRID 1908968Notes

Reaction equation

HRID 1908968 reaction equation
[C:1]([O:5][CH2:6][C@@H:7]1[C:12](=[O:13])[NH:11][CH2:10][CH2:9][N:8]1[C:14](=[O:38])[CH2:15][C@H:16]([NH:27]C(=O)OCC1C=CC=CC=1)[CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>CO.[Pd]>[NH2:27][C@H:16]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26])[CH2:15][C:14]([N:8]1[CH2:9][CH2:10][NH:11][C:12](=[O:13])[C@H:7]1[CH2:6][O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:38]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 131731066HCID 131731066, compound

Product 1

HCID 25022354EvogliptinYield 70.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

65.7 g of benzyl(R)-4-[(R)-2-(t-butoxymethyl)-3-oxopiperazine-1-yl]-4-oxo-1-(2,4,5-trifluorophenyl)butane-2-ylcarbamate of the above Step 1 was dissolved in 409 mL of methanol; a solution in which 13.1 g of palladium/carbon was wetted with 92 ml of ethyl acetate was added; and then stirred for 2 hours under hydrogen pressure of 15 bar. The resulting reaction solution was filtered with diatomite, and then concentrated under reduced pressure to obtain 34.8 g of a title compound.

Workup

  1. additionwas added
  2. customThe resulting reaction solution
  3. filtrationwas filtered with diatomite
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b76fc30afcf4e26b4832e610faca6b8
Source dataset
uspto-grants-2013_12
Patent number
US08598347B2

Reaction notes

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