Hydrochloric Acid → HCID 10289356, compound

HRID 1243966Notes

Reaction equation

HRID 1243966 reaction equation
[Na].[NH2:2][C:3]([NH2:5])=[O:4].C[O:7][CH2:8][C:9]([O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[O:35][CH:36]=[C:37]([C:39]4[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=4)[N:38]=3)=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)([C:15]([O:17][CH2:18]C)=O)[C:10](OCC)=[O:11].[OH-].[Na+].Cl>C(O)C.C(OCC)C.O>[CH3:18][O:17][CH2:15][C:9]1([O:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[O:35][CH:36]=[C:37]([C:39]5[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=5)[N:38]=4)=[CH:30][CH:29]=3)=[CH:25][CH:26]=2)[C:10](=[O:11])[NH:5][C:3](=[O:4])[NH:2][C:8]1=[O:7]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1176UreaHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 21931137HCID 21931137, compound

Product 1

HCID 10289356HCID 10289356, compoundYield 9.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium (210 mg, 9.1 mmol) was dissolved in dry ethanol (18 mL). Urea (328 mg, 5.46 mmol) and diethyl 2-(Methoxy-methyl)-2-{4-[4-(4-(4-fluorophenyl)-oxazol-2-yl)-phenoxy]-phenoxy}-malonate (1.0 g, 1.82 mmol) were added and the solution refluxed for 6 hours. The cooled mixture was diluted with ethyl ether and was with water and 2N sodium hydroxide solution. The combined aqueous layers were acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Filtration and concentration gave 179 mg of crude product which was chromatographed yielding 86 mg of the title compound as a white solid. LC-MS (m/z, APCI): 518 [M+H]+.

Workup

  1. temperaturethe solution refluxed for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration
  6. customgave 179 mg of crude product which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-10be906c3eeb49c99498e03f2072e2a6
Source dataset
uspto-grants-2006_10
Patent number
US07119201B2

Reaction notes

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