Diisopropylcarbodiimide → sodium 2-[[8-[3-[3-[(4-chlorophenyl)methylcarbamoyl]-8-fluoro-4-oxo-1H-quinolin-6-yl]propoxy]-8-oxooctanoyl]-methylamino]ethanesulfonate

HRID 2290044Notes

Reaction equation

HRID 2290044 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:4][CH:3]=1.[CH2:28]([NH+:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C.C(N=C=N[CH:41]([CH3:43])[CH3:42])(C)C.[S:44]([O-:48])([O-])(=[O:46])=[O:45].[Na+:49].[Na+].C(Cl)(Cl)Cl.[CH2:55]([OH:59])[CH2:56][CH2:57]C.C[OH:61]>CN(C1C=CN=CC=1)C.C(#N)C.C1COCC1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][CH2:23][O:24][C:55](=[O:59])[CH2:56][CH2:57][CH2:43][CH2:41][CH2:42][CH2:32][C:31]([N:30]([CH3:28])[CH2:33][CH2:34][S:44]([O-:48])(=[O:46])=[O:45])=[O:61])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:26][CH:27]=1.[Na+:49]

Participants

9

Reactant 5

HCID 12734DiisopropylcarbodiimideHCID 24436Sodium SulfateHCID 1385867TriethylammoniumHCID 86755573Chloroform butanol methanolHCID 178522910HCID 178522910, compound

Product 1

HCID 178484780sodium 2-[[8-[3-[3-[(4-chlorophenyl)methylcarbamoyl]-8-fluoro-4-oxo-1H-quinolin-6-yl]propoxy]-8-oxooctanoyl]-methylamino]ethanesulfonate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 21956068Chloroform tetrahydrofuranSolvent

Procedure

To a stirred mixture of 78 mg of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-quinolinecarboxamide from Example No. 110, 27 mg of DMAP, and 0.46 mL of a 0.65 M solution of suleptanic acid triethylammonium salt in acetonitrile, in 1 mL of 1:1 THF-chloroform, was added 38 μL of diisopropylcarbodiimide. The solution was stirred for 18 h, then concentrated under reduced pressure. Flash chromatography of the residue on silica using 5-15% methanol in dichloromethane provided a solid. This was dissolved in chloroform-butanol-methanol, and the solution stirred with saturated aqueous sodium sulfate. The organic phase was filtered through anhydrous sodium sulfate and concentrated under reduced pressure to afford 121 mg of the title compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customFlash chromatography of the residue on silica using 5-15% methanol in dichloromethane provided a solid
  3. filtrationThe organic phase was filtered through anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d632bc8a2ab47c8a40a79fd73c3f0ff
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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