Dimethyl Sulfoxide → HCID 58492492, compound

HRID 1874054Notes

Reaction equation

HRID 1874054 reaction equation
I(OC(=O)C1C=CC=CC=1)(=O)=O.CS(C)=O.[F:17][C:18]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[C:24]2[C:19]=1[C:20](=[O:49])[C:21]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)=[CH:22][N:23]2[CH2:32][CH2:33][S:34]([CH2:37][CH2:38][CH2:39][OH:40])(=[O:36])=[O:35].O>C(OCC)(=O)C>[F:17][C:18]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[C:24]2[C:19]=1[C:20](=[O:49])[C:21]([C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=1)=[CH:22][N:23]2[CH2:32][CH2:33][S:34]([CH2:37][CH2:38][CH:39]=[O:40])(=[O:35])=[O:36]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 58492443HCID 58492443, compoundHCID 86658927HCID 86658927, compound

Product 1

HCID 58492492HCID 58492492, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

O-iodoxybenzoic acid (IBX, 1.9 g, 6.78 mmol) was added to a dimethyl sulfoxide (DMSO) solution (3 ml) of 5-fluoro-1-[2-(3-hydroxypropane-1-sulfonyl)ethyl]-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (2.7 g, 5.65 mmol) and stirred overnight at room temperature. Water and ethyl acetate were added to the reaction mixture. Subsequently, insoluble matter was filtered off, and the filtrate was then separated. The thus-obtained organic layer was washed with water and concentrated under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=2:1→0:1). The purified material was concentrated to dryness under reduced pressure, giving a white powder of 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethanesulfonyl}propionaldehyde (1.8 g, yield: 67%).

Workup

  1. filtrationSubsequently, insoluble matter was filtered off
  2. customthe filtrate was then separated
  3. washThe thus-obtained organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified
  6. concentrationThe purified material was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6dfd38149be84178989464524eb699b0
Source dataset
uspto-grants-2012_11
Patent number
US08304546B2

Reaction notes

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