Ethanol → HCID 66636857, compound

HRID 1094182Notes

Reaction equation

HRID 1094182 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-ae3d9a7f5ebd429f8071cb405e597ad0
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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