Hydrochloric Acid → (2S)-2-(4-chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester
반응식
[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]참가 물질
6
반응물 4
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- 25 °C
실험 절차
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]+.
후처리
- 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)
출처 및 근거
- ORD 기록
- ord-a36093cf7f47453992a151119d72c4b1
- 출처 데이터셋
- uspto-grants-2009_06
- 특허 번호
- US07550629B2
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