Water → D-Tartrate

HRID 394846Notes

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

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-d58e25df84064c1c874ffb963f579069
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603002B2

Reaction notes

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