Ethanol → HCID 66636857, compound

HRID 469223Notes

Reaction equation

HRID 469223 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:33])[C:13](/[CH:23]=[CH:24]/[P:25](=[O:32])([O:29]CC)[O:26]CC)=[CH:14][N:15]3[CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:10][C:9]=2[F:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[Si](C)(C)C.C(O)C>C(Cl)(Cl)Cl>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:33])[C:13](/[CH:23]=[CH:24]/[P:25](=[O:26])([OH:32])[OH:29])=[CH:14][N:15]3[CH:18]([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:10][C:9]=2[F:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 86633050HCID 86633050, compound

Product 1

HCID 66636857HCID 66636857, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

13 g of diethyl {(E)-2-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]vinyl}phosphonate was dissolved in 150 ml of chloroform, and 27.2 ml of bromotrimethylsilane was added, followed by overnight stirring at room temperature. Ethanol was added to the reaction mixture, followed by concentration under a reduced pressure. Aqueous 1 M sodium hydroxide solution and ether were added to the resulting residue to carry out layer separation operation. Concentrated hydrochloric acid was added to the aqueous layer, followed by stirring at room temperature for 2 hours. Then, the insoluble materials were collected by filtration and washed with water to obtain 10.32 g of {(E)-2-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]vinyl}phosphonic acid.

Workup

  1. concentrationfollowed by concentration under a reduced pressure
  2. additionAqueous 1 M sodium hydroxide solution and ether were added to the resulting residue
  3. customlayer separation operation
  4. additionConcentrated hydrochloric acid was added to the aqueous layer
  5. stirringby stirring at room temperature for 2 hours
  6. filtrationThen, the insoluble materials were collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-bb26c177d12d42eeb25ebcb526f73e57
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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