Hydrochloric Acid → Ethyl 3-{[(4-([1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}phenyl)carbonyl](methyl)amino}propanoate

HRID 2091135Notes

Reaction equation

HRID 2091135 reaction equation
Cl[CH:2]([C:7]1[O:8][C:9]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:10]=2[C:11]=1[CH3:12])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]([CH3:36])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:22][CH:21]=1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)C=O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:9]2[O:8][C:7]([CH:2]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([N:28]([CH3:36])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:24][CH:25]=3)[CH2:3][CH:4]([CH3:6])[CH3:5])=[C:11]([CH3:12])[C:10]=2[CH:13]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 46941342Ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoateHCID 667782182-(1-Chloro-3-methylbutyl)-5-methoxy-3-methyl-1-benzofuran

Product 1

HCID 66777018Ethyl 3-{[(4-([1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}phenyl)carbonyl](methyl)amino}propanoateYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(1-chloro-3-methylbutyl)-5-methoxy-3-methyl-1-benzofuran (380 mg) synthesized in Example A92(2), ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoate (370 mg) synthesized in Example 2(2), sodium iodide (443 mg), sodium carbonate (314 mg) and N,N-dimethylformamide (10 mL) was stirred at 80° C. for 5 hr. 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 (60% ethyl acetate/hexane) to give the title object compound (350 mg, 51%) as a yellow oil.

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 (60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-873fc695a03f45729e92e07bb9620fe3
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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