Hydrochloric Acid → Saxagliptin hydrochloride

HRID 1960059Notes

Reaction equation

HRID 1960059 reaction equation
[CH2:1]1[C@@H:6]([C:7]#[N:8])[N:5]([C:9]([C@@H:11]([NH2:23])[C:12]23[CH2:21][C:19]4([OH:22])[CH2:20][CH:14]([CH2:15][CH:16]([CH2:18]4)[CH2:17]2)[CH2:13]3)=[O:10])[C@@H:4]2[C@H:2]1[CH2:3]2.O.[ClH:25]>C(O)CCC.C(OC(=O)C)CCC>[CH2:1]1[C@@H:6]([C:7]#[N:8])[N:5]([C:9]([C@@H:11]([NH2:23])[C:12]23[CH2:21][C:19]4([OH:22])[CH2:20][CH:14]([CH2:15][CH:16]([CH2:18]4)[CH2:17]2)[CH2:13]3)=[O:10])[C@@H:4]2[C@H:2]1[CH2:3]2.[ClH:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53297473945667-22-1

Product 1

HCID 49800073Saxagliptin hydrochloride

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 31272Butyl AcetateSolvent

Procedure

Saxagliptin monohydrate, form H-1 (2 g) was suspended in 15 ml of 1-butanol and a solution of 0.591 ml of conc. HCl in 15 ml of n-butylacetate (“BuOAc”) was added dropwise. The obtained suspension was analyzed by PXRD and polymorphically pure form Z was found to have been obtained. The suspension was stirred at room temperature for 30 min and then for additional 30 min in an ice bath. The suspension was then filtered, yielding 1.879 g of Saxagliptin HCl. PXRD is shown in FIG. 12.

Workup

  1. customto have been obtained
  2. waitfor additional 30 min in an ice bath
  3. filtrationThe suspension was then filtered

Sources & evidence

ORD record
ord-3646da33bd1540f9b30c7aa3078b36d2
Source dataset
uspto-grants-2013_04
Patent number
US08410288B2

Reaction notes

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