Water → D-Tartrate
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]12[C:16](=[O:17])[N:15]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:14](=[O:23])[N:9]1[CH2:10][CH2:11][NH:12][CH2:13]2.O.[C:25]([OH:34])(=[O:33])[C@H:26]([C@@H:28]([C:30]([OH:32])=[O:31])[OH:29])[OH:27]>CC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C@:8]12[C:16](=[O:17])[N:15]([CH2:18][C:19]([F:21])([F:22])[F:20])[C:14](=[O:23])[N:9]1[CH2:10][CH2:11][NH:12][CH2:13]2.[C:30]([C@H:28]([C@@H:26]([C:25]([O-:34])=[O:33])[OH:27])[OH:29])([O-:32])=[O:31]Participants
6
Reactant 3
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 56 °C
Procedure
To a solution of 8a-pyridin-2-ylmethyl-2-(2,2,2-trifluoro-ethyl)-tetrahydro-imidazo[1,5-a]pyrazine-1,3-dione (prepared according to the method described in Step 6, 106 g, 0.325 mol) in acetone (2120 mL) and water (212 mL) was added D-tartaric acid (48.46 g, 0.325 mol). White precipitate formed and it was granulated for 3 hours. The solids were collected by suction filtration and washed with acetone. The solvent damp solids were placed in acetone (1000 mL) and stirred at 56° C. overnight. The solids were collected by suction filtration the next morning and dried to give 56 g of the chiral title compound as the D-tartrate salt (73% yield of theory). Chiral HPLC showed an optical purity of 98:2.
Workup
- customWhite precipitate
- customformed
- filtrationThe solids were collected by suction filtration
- washwashed with acetone
- filtrationThe solids were collected by suction filtration the next morning
- customdried
Sources & evidence
- ORD record
- ord-93c4a1f94a634f4cb2339bcf0d6d264e
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06686471B2
Reaction notes
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