Sodium Hydroxide → HCID 16065394, compound

HRID 2425519Notes

Reaction equation

HRID 2425519 reaction equation
[CH3:1][S:2]([CH2:4][CH2:5][C:6]1[C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]([NH:18][C@H:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:20][CH3:21])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:3].C1C=C(Cl)C=C(C(OO)=[O:42])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl.O>[CH3:1][S:2]([CH2:4][CH2:5][C:6]1[C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]([NH:18][C@H:19]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:20][CH3:21])=[O:17])=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:42])=[O:3]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 53325403HCID 53325403, compound

Product 1

HCID 16065394HCID 16065394, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 3-[2-(methylsulfinyl)ethyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (12) (60 mg, 0.13 mmol) in CH2Cl2 at 0° C. was added MCPBA (70-75%, 36 mg, 0.16 mol). The cooling bath was removed and reaction stirred for 2 h, then sodium thiosulfate (1.2 eq.) and H2O (1 mL) were added and suspension stirred until all solids had dissolved. Aqueous 1 N NaOH (1 mL) and CH2Cl2 (2 mL) were then added, the layers shaken together, separated, the organics dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (5-20% EtOAc/CH2Cl2) to give the desired product (40 mg, 65% yield) as a solid. 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.12 (d, J=8.2 Hz, 1H), 7.78-7.65 (m, 2H), 7.56-7.26 (m, 11H), 6.31 (d, J=7.7 Hz, 1H), 5.23 (q, J=7.6 Hz, 1H), 3.36-2.88 (m, 4H), 2.45-2.34 (m, 3H), 2.16-1.88 (m, 2H), 1.04 (t, J=7.4 Hz, 3H); HRMS m/z 473.1878, calcd 473.1899.

Workup

  1. customThe cooling bath was removed
  2. customreaction
  3. stirringsuspension stirred until all solids
  4. dissolutionhad dissolved
  5. stirringthe layers shaken together
  6. customseparated
  7. dry with materialthe organics dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (5-20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-08e49103f3c64570a06b9bc8e6318972
Source dataset
uspto-grants-2011_06
Patent number
US07964733B2

Reaction notes

Loading…