Trifluoroacetic acid → 5-([4-[2-(4-Methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)oxazolidine-2,4-dione
Reaction equation
FC(F)(F)C(O)=O.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:15]2[C:19](=[O:20])[CH:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([O:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:33][CH:32]=4)=[CH:24][CH:23]=3)[O:17][C:16]2=[O:42])C=CC=CC=1>ClCCl>[CH3:41][S:38]([O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][CH2:29][O:28][C:25]2[CH:26]=[CH:27][C:22]([CH2:21][CH:18]3[O:17][C:16](=[O:42])[NH:15][C:19]3=[O:20])=[CH:23][CH:24]=2)=[CH:36][CH:35]=1)(=[O:39])=[O:40]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1 ml trifluoroacetic acid was added to a solution of 0.214 g (0.33 mmole) 3-triphenylmethyl-5-([4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)oxazolidine-2,4-dione in 10 ml dichloromethane. After stirring for 45 minutes at room temperature 20 ml more of dichloromethane was added, the reaction mixure was washed twice with water, dried (sodium sulfate) and the solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using heptane:ethyl acetate:acetic acid (10:10:1) as eluent to give 0.118 g (yield 88%) of 5-([4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl]methyl)oxazolidine-2,4-dione.
Workup
- additionwas added
- washthe reaction mixure was washed twice with water
- dry with materialdried (sodium sulfate)
- customthe solvent was evaporated in vacuo
- customThe crude product was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-293df3e401174385b38b570f7984d74c
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288096B1
Reaction notes
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