Hydrochloric Acid → Saxagliptin hydrochloride

HRID 1960061Notes

Reaction equation

HRID 1960061 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.[ClH:24].C(OCCCC)(=O)C>C(O)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:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31272Butyl AcetateHCID 11243969Saxagliptin

Product 1

HCID 49800073Saxagliptin hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of Saxagliptin (monohydrate, 4.5 g) in 1-butanol (“1-BuOH”, 68 ml) was warmed up to 40° C. and conc. Conc. HCl was added (1.258 ml). The resulting mixture was stirred at the same temperature for 30 min and a suspension was formed. The suspension was cooled to 20° C. and butyl acetate (“BuOAc” 68 ml) was added dropwise. The suspension was cooled to 0° C. and stirred for 2 h. The suspension was filtered, and the collected crystalline solid was washed with cool 1-BuOH/BuOAc (1/1) mixture yielding 3.92 g of the product. PXRD is shown in FIG. 18.

Workup

  1. customa suspension was formed
  2. temperatureThe suspension was cooled to 0° C.
  3. stirringstirred for 2 h
  4. filtrationThe suspension was filtered
  5. washthe collected crystalline solid was washed with cool 1-BuOH/BuOAc (1/1) mixture

Sources & evidence

ORD record
ord-a063e221e75d4ae1908084d657d01cef
Source dataset
uspto-grants-2013_04
Patent number
US08410288B2

Reaction notes

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