Hydrochloric Acid → HCID 12000653, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]=[C:11]([C:22]([OH:24])=[O:23])[CH2:10]2)=[CH:5][CH:4]=1>>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]=[C:11]([C:22]([OH:24])=[O:23])[CH2:10]2)=[CH:7][CH:8]=1Participants
Procedure
The residue obtained from the evaporation of the mother liquor obtained from the crystallisation of (R)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid with (+)-Cinchonine was treated with 6N HCl as described above for obtaining the free acid After evaporating the organic phase 23.63 g of a mixture with a theoretical composition of 13.34 mmoles of (R)-5-(4chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid and 47.34 mmoles of (S)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid were obtained. Said mixture, dissolved in 118 ml of acetone, was added on top of a solution of 18.7 g (47.4 mmoles) of brucine in 650 ml of acetone, stirred for a couple of minutes and left to crystallize at room temperature overnight. A creme-coloured solid was obtained that was filtered off and dried to yield 28 g (77.5% relative to the (S)-salt).
Workup
- customfor obtaining the free acid
Sources & evidence
- ORD record
- ord-65a1d9478f404d8c87b190e00a3f567a
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968582B2
Reaction notes
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