Lithium Hydroxide → Linagliptin

HRID 2172564Notes

Reaction equation

HRID 2172564 reaction equation
[CH3:1][C:2]#[C:3][CH2:4][N:5]1[C:9]([N:10]2[CH2:15][C@H:14]([NH2:16])[CH2:13][CH2:12][CH2:11]2)=[N:8][C:7]2[N:17]([CH3:35])[C:18]([N:20]([CH2:23][C:24]3[N:25]=[C:26]([CH3:34])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[N:33]=3)[C:21](=[O:22])[C:6]1=2)=[O:19].C([C@H]([C@@H](C([O-])=O)O)O)([O-])=O.[OH-].[Li+].[OH-].[Na+].[OH-].[K+]>O>[CH3:1][C:2]#[C:3][CH2:4][N:5]1[C:9]([N:10]2[CH2:15][C@H:14]([NH2:16])[CH2:13][CH2:12][CH2:11]2)=[N:8][C:7]2[N:17]([CH3:35])[C:18]([N:20]([CH2:23][C:24]3[N:25]=[C:26]([CH3:34])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[N:33]=3)[C:21](=[O:22])[C:6]1=2)=[O:19]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 131732960HCID 131732960, compound

Product 1

HCID 10096344Linagliptin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pure Linagliptin is isolated from Linagliptin-D-(−)-tartrate using water and a suitable base. The Linagliptin-D-(−)-tartrate solution is treated with a suitable base such as lithium hydroxide, sodium hydroxide, potassium hydroxide or the like. The base may be added in the form of a solution having about 1% to about 20% concentration. The resulted solution is treated with a water immiscible organic solvent and the organic layer containing linagliptin is separated and is washed with water and concentrated to produce pure Linagliptin.

Workup

  1. additionThe base may be added in the form of a solution
  2. concentrationabout 1% to about 20% concentration
  3. additionThe resulted solution is treated with a water immiscible organic solvent
  4. additionthe organic layer containing linagliptin
  5. customis separated
  6. washis washed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-06fe33393b9f49f9bf46fb377647bab4
Source dataset
uspto-grants-2015_06
Patent number
US09056112B2

Reaction notes

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