Hydrochloric Acid → Saxagliptin hydrochloride

HRID 1888969Notes

Reaction equation

HRID 1888969 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].O>CC(C)=O>[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 962WaterHCID 11243969Saxagliptin2×

Product 1

HCID 49800073Saxagliptin hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The Schiff base of Saxagliptin (compound M, 500 mg) was dissolved in acetone (4 ml), and HCl (0.131 ml, 36.5%) was added. The resulting suspension was stirred for 30 min. Water (0.6 ml) was added and continued stirring for additional 45 min. The suspension was then filtered yielding saxagliptin hydrochloride, form H2-1 (375 mg).

Workup

  1. stirringcontinued stirring for additional 45 min
  2. filtrationThe suspension was then filtered

Sources & evidence

ORD record
ord-52e542c5d9c84024a1a70de38da52a1c
Source dataset
uspto-grants-2013_08
Patent number
US08501960B2

Reaction notes

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