Water → (R)-N-((2-(2,2-Dimethoxypropyl)phenyl)(4-(trifluoromethyl)phenyl)-methyl)-2-methylpropane-2-sulfinamide

HRID 445360노트

반응식

HRID 445360 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:13][CH3:14])([O:11][CH3:12])[CH3:10].C([Li])(C)(C)C.[F:20][C:21]([F:37])([F:36])[C:22]1[CH:35]=[CH:34][C:25]([CH:26]=[N:27][S@@:28]([C:30]([CH3:33])([CH3:32])[CH3:31])=[O:29])=[CH:24][CH:23]=1.O>C1COCC1>[CH3:12][O:11][C:9]([O:13][CH3:14])([CH3:10])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:26]([C:25]1[CH:24]=[CH:23][C:22]([C:21]([F:36])([F:37])[F:20])=[CH:35][CH:34]=1)[NH:27][S@@:28]([C:30]([CH3:33])([CH3:32])[CH3:31])=[O:29]

참가 물질

6

반응물 4

HCID 962WaterHCID 595364291-Bromo-2-(2,2-dimethoxypropyl)benzeneHCID 68498575(R)-N-(4-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamideHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 59536312(R)-N-((2-(2,2-Dimethoxypropyl)phenyl)(4-(trifluoromethyl)phenyl)-methyl)-2-methylpropane-2-sulfinamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1-Bromo-2-(2,2-dimethoxypropyl)benzene (4.00 g, 15.43 mmol) was dissolved in 150 mL THF and tert-butyllithium (18.160 mL, 30.871 mmol) was added dropwise at −78° C. After addition a solution of (R)—N-(4-(trifluoromethyl)-benzylidene)-2-methylpropane-2-sulfinamide (8.5608 g, 30.871 mmol) in THF (10 mL) was added and stirring was continued for 10 min in the cold. The reaction was hydrolyzed with 50 mL water and the mixture was warmed to RT. TLC showed a 1:1 mixture of the 2 diastereomers. No attempt was undertaken to separate the isomers. Glass column chromatography provided the title compound as a mixture of diastereomers. MS (ESI, positive ion) m/z: 412.0 (M+1; hydrolysis of the dimethyl acetal to the corresponding ketone).

후처리

  1. additionwas added
  2. additiona 1:1 mixture of the 2 diastereomers
  3. customto separate the isomers

출처 및 근거

ORD 기록
ord-f3360a77b88b4df1b31c508ff3b4e934
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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