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

HRID 2091133Notes

Reaction equation

HRID 2091133 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]([NH:28][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]([NH:28][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 12469762Ethyl 3-(4-aminobenzamido)propanoateHCID 667782182-(1-Chloro-3-methylbutyl)-5-methoxy-3-methyl-1-benzofuran

Product 1

HCID 66778503Ethyl 3-{[(4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-3-methylbutyl]amino}phenyl)carbonyl]amino}propanoateYield 40%

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 above, ethyl 3-{[(4-aminophenyl)carbonyl]amino}propanoate (350 mg) synthesized in Example 1(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 (50% ethyl acetate/hexane) to give the title object compound (266 mg, 40%) 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 (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-54af93ef32914796abd40b89a29bd7db
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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