Sodium Hydroxide → HCID 66778672, compound

HRID 2091118Notes

Reaction equation

HRID 2091118 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH3:38])[CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[O:29])=[CH:24][CH:23]=3)[CH:18]([CH3:20])[CH3:19])=[C:14]([CH3:39])[C:13]=2[CH:40]=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:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]([N:30]([CH3:38])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:29])=[CH:26][CH:27]=3)[CH:18]([CH3:19])[CH3:20])=[C:14]([CH3:39])[C:13]=2[CH:40]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66778385HCID 66778385, compound2×

Product 1

HCID 66778672HCID 66778672, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 3-[{[4-({1-[5-(benzyloxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (1.25 g) optically resolved in the above-mentioned (1) was dissolved in ethanol (15 mL), 1N aqueous sodium hydroxide solution (4 mL) was added at room temperature, and the mixture was stirred at 50° C. for 0.5 hr. Ethanol was evaporated under reduced pressure, 1N hydrochloric acid (4 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 (1.08 g, 93%, 99.9% ee) as a colorless solid.

Workup

  1. customEthanol was evaporated under reduced pressure, 1N hydrochloric acid (4 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 (1.08 g, 93%, 99.9% ee) as a colorless solid

Sources & evidence

ORD record
ord-2fae5941b1684ccca066b21d780dc862
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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