Ethanol → HCID 16065393, compound

HRID 2425516Notes

Reaction equation

HRID 2425516 reaction equation
[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]

Participants

4

Reactant 2

HCID 702EthanolHCID 16065392HCID 16065392, compound

Product 1

HCID 16065393HCID 16065393, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a0cbb9396c964bd8a780e1ea7d37977f
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

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