Sodium Hydroxide → HCID 67490653, compound

HRID 2091352Notes

Reaction equation

HRID 2091352 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]([CH3:39])[CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])=[O:30])=[CH:25][CH:24]=3)[CH2:18][CH:19]([CH3:21])[CH3:20])=[C:14]([CH3:40])[C:13]=2[CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]([N:31]([CH3:39])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:30])=[CH:27][CH:28]=3)[CH2:18][CH:19]([CH3:21])[CH3:20])=[C:14]([CH3:40])[C:13]=2[CH:41]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66778233HCID 66778233, compound2×

Product 1

HCID 67490653HCID 67490653, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-[{[4-({1-[5-(benzyloxy)-3-methyl-1-benzofuran-2-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (0.46 g) synthesized in the above-mentioned (4) was dissolved in ethanol (5 mL), 1N aqueous sodium hydroxide solution (1.5 mL) was added to the solution at room temperature, and the mixture was stirred at room temperature for 0.5 hr. Ethanol was evaporated under reduced pressure, 1N hydrochloric acid (1.5 mL) was added to the residue, 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 washed with ethanol-water to give the title object compound (0.45 g, quantitative) as a colorless solid.

Workup

  1. customEthanol was evaporated under reduced pressure, 1N hydrochloric acid (1.5 mL)
  2. additionwas added to the residue
  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. washThe residue was washed with ethanol-water
  8. customto give the title object compound (0.45 g, quantitative) as a colorless solid

Sources & evidence

ORD record
ord-85dd9692f1764031890b922cb7a241b5
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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