2-Acetamidoethyl (2R)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetate → Halofenate
Reaction equation
[C:1]([NH:4][CH2:5][CH2:6][O:7][C:8](=[O:28])[C@@H:9]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)(=[O:3])[CH3:2]>C(OC(C)C)(C)C>[C:1]([NH:4][CH2:5][CH2:6][O:7][C:8](=[O:28])[CH:9]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=1)(=[O:3])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 44 °C
Procedure
(−)-(4-Chloro-phenyl)-(R)-(3-trifluoromethyl-phenoxy)-acetic acid 2-acetylamino-ethyl ester (90.0 g) was dissolved in diisopropylether (900 mL) at 55° C. The resulting mixture was polish filtered, the solution cooled to 44° C. over about 20 minutes and seeded. The resulting mixture was stirred for 1 hour at 44° C., cooled to 35° C. over 4 hours, then stirred at 35° C. for 2 hours to yield a thick suspension. The suspension was cooled to −5° C. over about 5 hours and then stirred at −5° C. The resulting crystals were filtered off with a centrifuge and washed with precooled (−5° C.) diisopropylether (100 mL). The wet product was dried at 30° C. to yield the title compound as a white crystalline solid, more specifically as white crystals, needles.
Workup
- filtrationfiltered
- temperaturecooled to 35° C. over 4 hours
- stirringstirred at 35° C. for 2 hours
- customto yield a thick suspension
- temperatureThe suspension was cooled to −5° C. over about 5 hours
- stirringstirred at −5° C
- filtrationThe resulting crystals were filtered off with a centrifuge
- washwashed with precooled (−5° C.) diisopropylether (100 mL)
- customThe wet product was dried at 30° C.
Sources & evidence
- ORD record
- ord-0590b7d42d60422bb71c9bf54c95b6e0
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541614B2
Reaction notes
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