Triethylamine → HCID 20306530, compound

HRID 1732482Notes

Reaction equation

HRID 1732482 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH2:9][CH:10]([NH2:14])[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2].[C:18]([O:22][C:23](ON=C(C1C=CC=CC=1)C#N)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[C:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH2:9][CH:10]([NH:14][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 516892Sodium BicarbonateHCID 20306541HCID 20306541, compound

Product 1

HCID 20306530HCID 20306530, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

DL-4-(m-Acetylphenoxy)-2-aminobutyric acid (4.30 g.), 2-tert-butoxycarbonyloxyimino-2-phenylacetonitrile (4.92 g.) and triethylamine (2.53 g.) were dissolved in a mixture of dioxane (22 ml.) and water (22 ml.), whereafter the mixture was stirred at ambient temperature for 2.5 hours. The dioxane was removed by evaporation from the reaction mixture under reduced pressure to give an aqueous solution which was adjusted to pH 8-9 with an aqueous sodium bicarbonate. The resultant aqueous solution was washed with ethyl acetate and adjusted to pH 2 with 10% hydrochloric acid under ice-cooling. This solution was extracted three times with ethyl acetate, and the extract was washed with water and then dried over magnesium sulfate. The solvent was removed by evaporation from the solution under reduced pressure to give DL-4-(m-acetylphenoxy)-2-tert-butoxycarbonylaminobutyric acid (2.03 g.).

Workup

  1. customThe dioxane was removed by evaporation from the reaction mixture under reduced pressure
  2. customto give an aqueous solution which
  3. washThe resultant aqueous solution was washed with ethyl acetate
  4. temperaturecooling
  5. extractionThis solution was extracted three times with ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed by evaporation from the solution under reduced pressure

Sources & evidence

ORD record
ord-a078bf0a0723480e90fe53785260fc59
Source dataset
uspto-grants-1980_12
Patent number
US04237305

Reaction notes

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