Acetic Anhydride → HCID 70179449, compound

HRID 2229499Notes

Reaction equation

HRID 2229499 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C@@H:5]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:22])[C@@H:5]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:23](=[O:25])[CH3:24])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10638537Ethyl 4-amino-N-(tert-butoxycarbonyl)-L-phenylalaninate

Product 1

HCID 70179449HCID 70179449, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)-Ethyl-2-tert-butyloxycarbonylamino-3-(4-aminophenyl)propionate (0.10 g, 0.31 mmol) was dissolved in ethyl acetate (4 mL). Acetic anhydride (1 eq, 0.31 mmol, 0.030 mL) was added and the pale peach solution was heated to reflux, stirring at this temperature for 6.5 hours. The heating bath was removed and the flask allowed to cool to room temperature overnight. The solution was then poured into aqueous saturated NaHCO3 and extracted. The organic portion was washed again with sat. NaHCO3, then it was dried over MgSO4, filtered, and concentrated. Trituration with diethyl ether induced precipitation of a pale pink solid (0.09 g, 84%).

Workup

  1. temperaturethe pale peach solution was heated
  2. temperatureto reflux
  3. customThe heating bath was removed
  4. additionThe solution was then poured into aqueous saturated NaHCO3
  5. extractionextracted
  6. washThe organic portion was washed again with sat. NaHCO3
  7. dry with materialit was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customprecipitation of a pale pink solid (0.09 g, 84%)

Sources & evidence

ORD record
ord-0fca7ea42e6d4d849dd5853ad669fe03
Source dataset
uspto-grants-2002_07
Patent number
US06420424B1

Reaction notes

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