Hydrochloric Acid → HCID 57671810, compound

HRID 871992Notes

Reaction equation

HRID 871992 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:36])=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[C:27]([C:29]([O:31]C)=[O:30])[CH:26]=[CH:25][C:24]=2[O:33][CH3:34])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2.C(OCC)(=O)C.Cl>O1CCCC1.CO.[OH-].[Na+]>[C:29]([C:27]1[CH:26]=[CH:25][C:24]([O:33][CH3:34])=[C:23]([C:10]2[C:9]([CH2:8][O:7][C:6]3[CH:35]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH3:36])=[C:18]3[C:13]([NH:14][C:15]([CH3:22])([CH3:21])[C:16](=[O:20])[N:17]3[CH3:19])=[CH:12][CH:11]=2)[CH:28]=1)([OH:31])=[O:30]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 57671881HCID 57671881, compound

Product 1

HCID 57671810HCID 57671810, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

8-(5-Fluoro-2-methylphenoxymethyl)-7-(2-methoxy-5-methoxycarbonylphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 6-37, 50.5 mg, 0.103 mmol) was dissolved in mixed solvent of tetrahydrofuran (1 mL) and methanol (1 mL), and 4N aqueous sodium hydroxide solution (0.5 mL) was added thereto and stirred at room temperature overnight. Ethyl acetate (15 mL) and 0.25N aqueous HCl solution (20 mL) were added to the reaction mixture and partitioned. The organic layer was washed with saturated brine (15 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate). The obtained materials were filtered with chloroform (3 mL) to give the titled compound (20.3 mg) as a pale yellow solid. (Yield 42%)

Workup

  1. additionwas added
  2. custompartitioned
  3. washThe organic layer was washed with saturated brine (15 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  7. filtrationThe obtained materials were filtered with chloroform (3 mL)

Sources & evidence

ORD record
ord-d523df886eff4d41bfcb0014d02eb0e5
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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