Ethanol → HCID 16065393, 화합물

HRID 2425516노트

반응식

HRID 2425516 반응식
[CH3:1][S:2][CH2:3][C:4]1[C:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([NH:16][C@H:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18][CH3:19])=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2.CC[OH:34]>O>[CH3:1][S:2]([CH2:3][C:4]1[C:5]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:6][C:7]2[C:12]([C:13]=1[C:14]([NH:16][C@H:17]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:18][CH3:19])=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:34]

참가 물질

4

반응물 2

HCID 702EthanolHCID 16065392HCID 16065392, 화합물

생성물 1

HCID 16065393HCID 16065393, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 3-[(methylthio)methyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (9)(1.7 g, 3.98 mmol) in EtOH (40 mL) was cooled to 0° C., and to this, with stirring, was added a solution of NaIO4 (1.02 g, 4.78 mmol) in H2O (20 mL). The cooling bath was removed and reaction allowed to stir for 3 h, and then concentrated under reduced pressure to remove most of the EtOH. It was then diluted with EtOAc, washed with H2O (containing some NaCl to reduce emulsion), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10-35% EtOAc/CH2Cl2) to give the desired products (two diastereomers) each as a solid.

후처리

  1. customThe cooling bath was removed
  2. customreaction
  3. stirringto stir for 3 h
  4. concentrationconcentrated under reduced pressure
  5. customto remove most of the EtOH
  6. additionIt was then diluted with EtOAc
  7. washwashed with H2O (
  8. additioncontaining some NaCl
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel chromatography (10-35% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-a0cbb9396c964bd8a780e1ea7d37977f
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964733B2

반응 노트

불러오는 중…