Ethyl Acetate → HCID 20306523, compound

HRID 1732480Notes

Reaction equation

HRID 1732480 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][CH2:8][CH2:9][CH:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11]([O-:13])=[O:12])(=[O:3])C.[Se](=O)=O.[C:28](=[O:31])([OH:30])[O-].[Na+].[C:33](OCC)(=O)C>N1C=CC=CC=1>[C:18]([O:17][C:15]([NH:14][CH:10]([C:11]([O:13][CH3:33])=[O:12])[CH2:9][CH2:8][O:7][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[C:28]([OH:30])=[O:31])[CH:24]=[CH:23][CH:22]=1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24007Selenium DioxideHCID 516892Sodium BicarbonateHCID 86737375HCID 86737375, compound

Product 1

HCID 20306523HCID 20306523, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

Methyl DL-4-(m-acetylphenoxy)-2-tert-butoxycarbonylaminobutyrate (2.21 g.) was dissolved in pyridine (10 ml.), and to the solution was added selenium dioxide (1.11 g.), whereafter the solution was stirred at 90° C. for 4.5 hours. The reaction mixture was filtered and the filter cake was washed with ethyl acetate. These washings and the filtrate were combined and evaporated to dryness under reduced pressure to give a residue, which was poured into a mixture of an aqueous sodium bicarbonate and ethyl acetate. The insoluble materials were removed by filtration and the filtrate was adjusted to pH 2 with 10% hydrochloric acid. This aqueous solution was extracted twice with ethyl acetate, and the extract was washed with water and then dried over magnesium sulfate. The ethyl acetate was removed by evaporation from the solution under reduced pressure to give DL-m-(3-tert-butoxycarbonylamino-3-methoxycarbonylpropoxy)phenylglyoxylic acid (1.35 g.).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with ethyl acetate
  3. customevaporated to dryness under reduced pressure
  4. customto give a residue, which
  5. customThe insoluble materials were removed by filtration
  6. extractionThis aqueous solution was extracted twice with ethyl acetate
  7. washthe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customThe ethyl acetate was removed by evaporation from the solution under reduced pressure

Sources & evidence

ORD record
ord-cc592ce315ec4becb21786acc0f7ef28
Source dataset
uspto-grants-1980_12
Patent number
US04237305

Reaction notes

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