Acetone → Ticagrelor D-Tartrate

HRID 589828Notes

Reaction equation

HRID 589828 reaction equation
[CH3:1][CH2:2][CH2:3][S:4][C:5]1[N:6]=[C:7]([NH:25][C@H:26]2[C@H:28]([C:29]3[CH:30]=[CH:31][C:32]([F:36])=[C:33]([F:35])[CH:34]=3)[CH2:27]2)[C:8]2[N:13]=[N:12][N:11]([C@H:14]3[C@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([O:21][CH2:22][CH2:23][OH:24])[CH2:15]3)[C:9]=2[N:10]=1.CC(C)=O.[C:41]([OH:50])(=[O:49])[CH:42]([CH:44]([C:46]([OH:48])=[O:47])[OH:45])[OH:43]>CCCCCC>[CH3:1][CH2:2][CH2:3][S:4][C:5]1[N:6]=[C:7]([NH:25][C@H:26]2[C@H:28]([C:29]3[CH:30]=[CH:31][C:32]([F:36])=[C:33]([F:35])[CH:34]=3)[CH2:27]2)[C:8]2[N:13]=[N:12][N:11]([C@H:14]3[C@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([O:21][CH2:22][CH2:23][OH:24])[CH2:15]3)[C:9]=2[N:10]=1.[C:46]([C@H:44]([C@@H:42]([C:41]([O-:50])=[O:49])[OH:43])[OH:45])([O-:48])=[O:47]

Participants

5

Reactant 3

HCID 180AcetoneHCID 8752,3-Dihydroxybutanedioic AcidHCID 9871419Ticagrelor

Product 1

HCID 131734469Ticagrelor D-TartrateYield 93%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

Ticagrelor (0.5 g) and acetone (10 mL) were charged into a round bottom flask and the mixture was stirred at about 30° C. for about 15 minutes for clear solution. Then D (−)-tartaric acid (0.16 g) was added to the above reaction mixture at about 30° C. and mixture was stirred for overnight. To the clear solution, n-hexane (35 mL) was added and stirred for about 1 hour at 25-30° C. for solid separation. The solid was filtered, washed with n-hexane (5 mL) and dried to afford the title compound in about 93% yield having chiral HPLC purity of about 98%.

Workup

  1. stirringmixture was stirred for overnight
  2. stirringstirred for about 1 hour at 25-30° C. for solid separation
  3. filtrationThe solid was filtered
  4. washwashed with n-hexane (5 mL)
  5. customdried

Sources & evidence

ORD record
ord-6c81801d40bf4a72974c87d80fd2f295
Source dataset
uspto-grants-2016_01
Patent number
US09233966B2

Reaction notes

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