Trifluoroacetic acid → 2-[3-[(4-Chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propylamino]ethanol Hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH2:12][CH2:13][N:14]([CH2:22][CH2:23][OH:24])C(=O)OC(C)(C)C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH2:12][CH2:13][NH:14][CH2:22][CH2:23][OH:24])(=[O:10])=[O:9])=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
In dichloromethane (5 ml) was dissolved t-butyl N-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propyl]-N-(2-hydroxyethyl)carbamate (300 mg, 0.607 mmol) and trifluoroacetic acid (0.5 ml) was added dropwise to the resulting solution under ice cooling. After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. To the residue was added a 1N solution (5 ml) of hydrochloric acid in ethanol, followed by concentration under reduced pressure to give a white solid. The solid thus obtained was washed with diethyl ether, whereby the title compound (249 mg, 0.579 mmol, 95%) was obtained as a white powder.
Workup
- additionwas added dropwise to the resulting solution under ice cooling
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionTo the residue was added a 1N solution (5 ml) of hydrochloric acid in ethanol
- concentrationfollowed by concentration under reduced pressure
- customto give a white solid
- customThe solid thus obtained
Sources & evidence
- ORD record
- ord-d8c77c82efa5428886869e70779c5408
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399775B2
Reaction notes
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