Triethyl phosphonoacetate → HCID 66636986, compound

HRID 469250Notes

Reaction equation

HRID 469250 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)[CH3:4].[CH:17]1([NH:23][C:24]2[CH:33]=[C:32]3[C:27]([C:28](=[O:44])[C:29]([O:39][CH2:40][C:41](=O)[CH3:42])=[CH:30][N:31]3[CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:26][C:25]=2[F:45])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl-].[NH4+]>C1COCC1>[CH:17]1([NH:23][C:24]2[CH:33]=[C:32]3[C:27]([C:28](=[O:44])[C:29]([O:39][CH2:40]/[C:41](/[CH3:42])=[CH:7]/[C:6]([O:5][CH2:3][CH3:4])=[O:16])=[CH:30][N:31]3[CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:26][C:25]=2[F:45])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66636993HCID 66636993, compound

Product 1

HCID 66636986HCID 66636986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 5 ml THF solution of 119 mg of 60% sodium hydride was added 598 μl of ethyl(diethoxyphosphoryl)acetate at 0° C., followed by stirring for 30 minutes. A 5 ml THF solution of 400 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(2-oxopropoxy)quinolin-4(1H)-one was added thereto at the same temperature, followed by stirring at room temperature for 2 hours. To the reaction mixture was added aqueous saturated ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 200 mg of ethyl (2E)-4-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}-3-methylbut-2-enoate.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4cef6eda25704786b25547bcc956017f
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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