Water → N-(5-Cyano-2-fluoro-4-hydroxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

HRID 17527노트

반응식

HRID 17527 반응식
[C:1]([C:3]1[C:4]([O:24]C)=[C:5]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]([F:16])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]=1[CH3:9])#[N:2].O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([C:3]1[C:4]([OH:24])=[C:5]([NH:17][C:18](=[O:23])[C:19]([CH3:20])([CH3:21])[CH3:22])[C:6]([F:16])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]=1[CH3:9])#[N:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86630868N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

생성물 1

HCID 86630869N-(5-Cyano-2-fluoro-4-hydroxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide수율 65%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide (I-237) (200 mg, 0.59 mmol) was dissolved in dichloromethane (5 ml), and under nitrogen atmosphere at −78° C., 1 M borondichloromethane tribromide solution (1.76 ml, 1.76 mmol) was dropwise added. With stirring, the solution was heated up to 0° C., taking 3 hours. At the same temperature, water with ice was gradually dropwise added to it, followed by stirring for 5 minutes. Further, an aqueous saturated sodium hydrogencarbonate solution was added to the solution to make pH=7. The solution was extracted twice with dichloromethane. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1) to obtain the entitled compound (125 mg, 65%) as a white solid.

후처리

  1. stirringby stirring for 5 minutes
  2. extractionThe solution was extracted twice with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-d4fee1ca6dbe461aab1205933531c6cc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

반응 노트

불러오는 중…