Hydrochloric Acid → HCID 66777276, compound

HRID 2091002Notes

Reaction equation

HRID 2091002 reaction equation
Cl[CH:2]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:6]=2[CH:7]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:28])=[CH:23][CH:22]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl.[OH-].[Na+]>C(O)C.O1CCCC1.CN(C)C(=O)C>[CH:14]1([CH:2]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:25][CH:26]=2)[C:3]2[O:4][C:5]3[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:6]=3[CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 12469762Ethyl 3-(4-aminobenzamido)propanoateHCID 66778151HCID 66778151, compound

Product 1

HCID 66777276HCID 66777276, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-[chloro(cyclohexyl)methyl]-5-methoxy-1-benzofuran (360 mg) synthesized above, ethyl 3-{[(4-aminophenyl)carbonyl]amino}propanoate (305 mg) synthesized in Example 1(2), sodium iodide (291 mg) and N,N-dimethylacetamide (10 mL) was added sodium carbonate (206 mg), and the mixture was stirred at 80° C. overnight. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=11:9, volume ratio) to give a yellow oil. To a mixture of the obtained oil, tetrahydrofuran (2.5 and ethanol (2.5 mL) was added 1N aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water (5 mL), and 1N hydrochloric acid (1 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (96.0 mg, 17%) as a yellow solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=11:9, volume ratio)
  8. customto give a yellow oil
  9. stirringthe mixture was stirred at room temperature for 4 hr
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. dissolutionthe residue was dissolved in water (5 mL)
  12. addition1N hydrochloric acid (1 mL) was added at 0° C
  13. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-56db820ec3d24afc85f2f00e0d3a3b94
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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