9-Fluorenylmethyl chloroformate → 7-(2-Methoxy-4-methoxymethoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 215820

Reaction equation

HRID 215820 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]([CH2:23][NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[C:21]2[C:16]([NH:17][C:18]([CH3:36])([CH3:35])[C:19](=[O:34])[N:20]2[CH3:33])=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+].[CH:42]1[C:54]2[CH:53]([CH2:55][O:56][C:57](Cl)=[O:58])[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[CH:45]=[CH:44][CH:43]=1>O1CCOCC1.O.C(OCC)(=O)C>[CH:42]1[C:54]2[CH:53]([CH2:55][O:56][C:57]([N:24]([CH2:23][C:22]3[C:13]([C:4]4[CH:5]=[CH:6][C:7]([O:9][CH2:10][O:11][CH3:12])=[CH:8][C:3]=4[O:2][CH3:1])=[CH:14][CH:15]=[C:16]4[C:21]=3[N:20]([CH3:33])[C:19](=[O:34])[C:18]([CH3:36])([CH3:35])[NH:17]4)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])=[O:58])[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 583371847-(2-Methoxy-4-methoxymethoxyphenyl)-8-(2-methoxyphenylaminomethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 583371967-(2-Methoxy-4-methoxymethoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

7-(2-Methoxy-4-methoxymethoxyphenyl)-8-(2-methoxyphenylaminomethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 8-4, 104 mg, 0.212 mmol) and sodium hydrogen carbonate (22.0 mg, 0.262 mmol) were dissolved in mixed solvent of 1,4-dioxane (1.5 mL) and water (1 mL), and 9-fluorenylmethoxycarbonyl chloride (60.3 mg, 0.233 mmol) was added thereto. After the reaction mixture was stirred at room temperature for 30 minutes, the mixture was diluted with ethyl acetate (50 mL). The mixture was washed with water (50 mL) and saturated brine (50 mL) successively, 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) to give the titled reference compound (149 mg) as a colorless amorphous product. (Yield 99%)

Workup

  1. additionwas added
  2. washThe mixture was washed with water (50 mL) and saturated brine (50 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-866bf2b13ee54ff893a67619538c690c
Source dataset
uspto-grants-2012_06
Patent number
US08193187B2

Linked notes

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