Hydrochloric Acid → (2S)-2-(4-chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([NH2:16])[CH:5]([CH2:11][C:12]([F:15])([F:14])[F:13])[CH2:6][C:7]([F:10])([F:9])[F:8].N1C=CC=CC=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.Cl>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([NH:16][S:31]([C:28]1[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=1)(=[O:33])=[O:32])[CH:5]([CH2:6][C:7]([F:9])([F:10])[F:8])[CH2:11][C:12]([F:15])([F:14])[F:13]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of (2S)-2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester (2.173 g, 8.14 mmol) and pyridine (1.97 mL, 24.4 mmol) in CH2Cl2 (15 mL) was added a solution of 4-chlorobenzenesulfonyl chloride (2.66 g, 12.2 mmol, 97% pure) in CH2Cl2 (7 mL). The reaction mixture was stirred at 25° C. for 4 h, then cooled to 0° C. 15 mL of 1N HCl was added followed by 10 mL of dichloromethane. The phases were separated. The organic phase was washed with 1N HCl (15 mL) and brine, dried over Na2SO4, and concentrated to afford 4.1 g of crude mixture as a yellow solid. The solids were recrystallized from heptane (14 mL) to afford 3.035 g of the title product (84% yield). Mass Spectrum (+ESI): 442 [M+H]+.
Workup
- temperaturecooled to 0° C
- customThe phases were separated
- washThe organic phase was washed with 1N HCl (15 mL) and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customto afford 4.1 g of crude mixture as a yellow solid
- customThe solids were recrystallized from heptane (14 mL)
Sources & evidence
- ORD record
- ord-a36093cf7f47453992a151119d72c4b1
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550629B2
Reaction notes
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