Acetic Anhydride → Benzyl 3-acetamido-4-oxopentanoate

HRID 1275360

Reaktionsgleichung

Reaktionsgleichung von HRID 1275360
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=O)=[O:10])=[CH:3][CH:2]=1.[CH2:17](N(CC)CC)C.[C:24](OC(=O)C)(=[O:26])[CH3:25].[OH-].[K+]>CN(C)C1C=CN=CC=1.O>[C:24]([NH:16][CH:12]([C:13](=[O:15])[CH3:17])[CH2:11][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:10])(=[O:26])[CH3:25]

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 1011864-(Phenylmethyl) hydrogen L-aspartate

Produkt 1

HCID 22220883Benzyl 3-acetamido-4-oxopentanoateAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

β-Benzyl L-aspartate (400 g, 1.79 mol) was suspended in triethylamine (748 ml, 5.37 mol) and acetic anhydride (676 ml, 7.16 mol) was dropwise added at 0° C. with stirring. After stirring for 30 minutes, 4-dimethylaminopyridine (20.0 g, 0.16 mol) was portionwise added under Ice-cooling. The mixture was stirred overnight at room temperature, and ice was added under ice-cooling. At the end of the exothermic process, water (700 ml) was added. A 7.5 N aqueous solution of potassium hydroxide was portionwise added to make its pH 9. The mixture was extracted three times with ethyl acetate (1,000 ml), and the organic layer was washed twice with 1 N hydrochloric acid (1,000 ml), twice with a saturated aqueous solution of sodium hydrogencarbonate (500 ml) and with saturated brine (500 ml) in order. The layer was dried over magnesium sulfate and concentrated to dryness to give 390 g of the title compound.

Aufarbeitung

  1. stirringAfter stirring for 30 minutes
  2. temperaturecooling
  3. stirringThe mixture was stirred overnight at room temperature
  4. additionice was added under ice-
  5. temperaturecooling
  6. extractionThe mixture was extracted three times with ethyl acetate (1,000 ml)
  7. washthe organic layer was washed twice with 1 N hydrochloric acid (1,000 ml), twice with a saturated aqueous solution of sodium hydrogencarbonate (500 ml) and with saturated brine (500 ml) in order
  8. dry with materialThe layer was dried over magnesium sulfate
  9. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-dab2a6a1d5474cea92e85df9fbe51737
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06160124

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