Hydrochloric Acid → Sitagliptin monohydrochloride

HRID 1942911Notes

Reaction equation

HRID 1942911 reaction equation
[CH:1]1[C:2]([CH2:10][C@@H:11]([NH2:28])[CH2:12][C:13]([N:15]2[CH2:27][C:19]3=[N:20][N:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[N:18]3[CH2:17][CH2:16]2)=[O:14])=[C:3]([F:9])[CH:4]=[C:5]([F:8])[C:6]=1[F:7].[ClH:29]>CC(O)C>[CH:1]1[C:2]([CH2:10][C@@H:11]([NH2:28])[CH2:12][C:13]([N:15]2[CH2:27][C:19]3=[N:20][N:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[N:18]3[CH2:17][CH2:16]2)=[O:14])=[C:3]([F:9])[CH:4]=[C:5]([F:8])[C:6]=1[F:7].[ClH:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 4369359Sitagliptin

Product 1

HCID 11476287Sitagliptin monohydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

Sitagliptin base (150 mg) was suspended in 2-propanol (2.5 mL). Hydrochloric acid (36 mg of 37% aqueous solution) was added and the mixture was stirred for one hour at ambient temperature and 2 hours at 40° C. The mixture was allowed to cool to ambient temperature and stirred for 24 hours before evaporation of the solvent.

Workup

  1. temperatureto cool to ambient temperature
  2. stirringstirred for 24 hours before evaporation of the solvent

Sources & evidence

ORD record
ord-4e49d55b5ffa489fb0b0fca2358982d5
Source dataset
uspto-grants-2013_03
Patent number
US08389724B2

Reaction notes

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