Water → (2R)-4-(3-Pyridyl)-2-benzoyloxy-1-(3'-cyanobiphenyl-4-yloxy)butane

HRID 1600914노트

반응식

HRID 1600914 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].C1(C)C=CC(S(O[CH2:28][C@H:29]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:30][CH2:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)(=O)=O)=CC=1.O>CN(C)C=O>[N:34]1[CH:35]=[CH:36][CH:37]=[C:32]([CH2:31][CH2:30][C@@H:29]([O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:28][O:15][C:12]2[CH:13]=[CH:14][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)=[CH:10][CH:11]=2)[CH:33]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 37790963-(4-Hydroxyphenyl)benzonitrileHCID 53780759(2R)-2-Benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate

생성물 1

HCID 53808556(2R)-4-(3-Pyridyl)-2-benzoyloxy-1-(3'-cyanobiphenyl-4-yloxy)butane수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Solid 3'-cyanobiphenyl-4-ol (0.20 g, Example 36b)) was added to a suspension of sodium hydride (60%, 0.049 g) in dimethylformamide (5 ml) and the resulting solution stirred for 30 minutes. Solid (2R)-2-benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.43 g) was then added and the mixture stirred at 60° C. for 2 hours. The mixture was cooled, poured into water (50 ml) and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained was purified by column chromatography over silica eluting with diethyl ether to give the sub-title compound as an oil (0.34 g).

후처리

  1. stirringthe mixture stirred at 60° C. for 2 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by column chromatography over silica eluting with diethyl ether

출처 및 근거

ORD 기록
ord-0b8d4c95eeaa43cf8c15ddc2afb1534a
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05977105

반응 노트

불러오는 중…