Isopropanol → HCID 12993946, compound
Reaction equation
FC(F)(F)C(O)(C)C(O)=O.CC(O)C.[C:15]1([C:21]2[CH:38]=[CH:37][C:24]([CH2:25][NH:26][CH:27]([CH3:36])[C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[C:15]1([C:21]2[CH:22]=[CH:23][C:24]([CH2:25][NH:26][C@H:27]([CH3:36])[C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])=[CH:37][CH:38]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2,46 g (15.56 mmol) of racemic 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid dissolved in a mixed solvent of 20.82 g of water and 16.65 g of 2-propanol at 55° C. was added at 55° C. to a solution of 2.80 g (7.85 mmol) of ()-N-(4-phenylbenzyl)-2,4-dichloro-α-methylbenzylamine in a mixed solvent of 20.78 g of water and 16.62 g of 2-propanol and the resulting solution was mixed under stirring. The solution was inoculated at 55° C. and then cooled to 25° C. under stirring over 1.5 hours and kept at the temperature for 2 hours. The precipitated crystals were collected by filtration and the collected crystals were washed with a mixed solvent of 2.50 g of water and 2.00 g of 2-propanol and dried to yield 2.75 g of (R)-N-(4-phenylbenzyl)-2,4-dichloro-α-methylbenzylamine salt of (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid with an optical purity of 97% ee.
Workup
- additionthe resulting solution was mixed
- customwas inoculated at 55° C.
- stirringunder stirring over 1.5 hours
- filtrationThe precipitated crystals were collected by filtration
- washthe collected crystals were washed with a mixed solvent of 2.50 g of water and 2.00 g of 2-propanol
- customdried
Sources & evidence
- ORD record
- ord-618d94cf35384946813e15ef1fed06f0
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06894190B2
Reaction notes
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