Dimethyl Sulfoxide → HCID 58492492, compound

HRID 68161Notes

Reaction equation

HRID 68161 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-c2227e4dca464d0e83706ae6e7fecd30
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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