Ether hydrochloride → Evogliptin hydrochloride

HRID 1660765Notes

Reaction equation

HRID 1660765 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:35])[CH2:15][C@H:16]([NH:27]C(=O)OC(C)(C)C)[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].[ClH:36].C(OCC)C>CO>[ClH:36].[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:35]

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 86641589HCID 86641589, compound

Product 1

HCID 25022353Evogliptin hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

97 mg of tert-butyl (R)-4-[(R)-2-(tert-butoxymethyl)-3-oxopiperazin-1-yl]-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate prepared in Step 8 was dissolved in 3 mL of methanol, followed by addition of 2 mL of 2N-hydrochloric acid/diethyl ether and stirring at room temperature for 3 hours. The reaction mixture was concentrated and dried under reduced pressure to afford 64 mg of the title compound as a foamy solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-3f10e5fc5ef445cc8fdbf936612c772e
Source dataset
uspto-grants-2011_10
Patent number
US08030315B2

Reaction notes

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