Water → Linagliptin

HRID 2172577Notes

Reaction equation

HRID 2172577 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.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 131732960HCID 131732960, compound

Product 1

HCID 10096344LinagliptinYield 103.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
28 °C

Procedure

Linagliptin-D-(−)-tartrate (45 gm), water (675 mL) and toluene (900 mL) were charged into 5000 mL round bottomed flask and stirred for 10 minutes at 28° C. The resulted solution was heated to 45° C. and 45 mL of 9% aqueous sodium hydroxide solution was added to the mixture at 45° C. (pH is 11.30) and maintained for 1 hour. Layers were separated and organic layer was washed with water (225 mL×2). Combined the organic layers and distilled off the organic layer under vacuum at 45° C. to give 35.4 gm of linagliptin.

Workup

  1. temperatureThe resulted solution was heated to 45° C.
  2. temperaturemaintained for 1 hour
  3. customLayers were separated
  4. washorganic layer was washed with water (225 mL×2)
  5. distillationdistilled off the organic layer under vacuum at 45° C.

Sources & evidence

ORD record
ord-0699d6478aa94de29de2d7acb9f45b2d
Source dataset
uspto-grants-2015_06
Patent number
US09056112B2

Reaction notes

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