Water → Ethyl 2-acetamido-3-oxobutanoate

HRID 1875108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875108
CN1CC[O:5][CH2:4][CH2:3]1.Cl.[NH2:9][CH:10]([C:16](=[O:18])[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(OC(=O)C)(=O)C.O>CN(C=O)C.C1COCC1>[C:4]([NH:9][CH:10]([C:16](=[O:18])[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:5])[CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 79724-MethylmorpholineHCID 13282897Ethyl 2-amino-3-oxobutanoate hydrochloride

Produkt 1

HCID 224840Ethyl 2-acetamido-3-oxobutanoateAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Methylmorpholine (0.41 mL, 3.7 mmol) was added dropwise via a syringe pump to a mixture of ethyl 2-amino-3-oxobutanoate hydrochloride (565 mg, 3.12 mmol) and acetic anhydride (0.35 mL, 3.7 mmol) in DMF (2 mL) and THF (4 mL) at RT under N2 over a period of 30 min. The reaction was stirred for 1 h and water was then added. It was extracted with EtOAc. The organic layer was washed with saturated sodium bicarbonate, HCl (1 N) and brine, dried over sodium sulfate and concentrated. The residue was purified by ISCO FC with 0-40% EtOAc in hexane to give the title compound (73 mg, 13%) as a light-yellow crystalline solid. 1H NMR (400 MHz, CDCl3-d) δ ppm 6.60 (s, 1H) 5.22 (d, J=6.59 Hz, 1H) 4.25 (q, J=6.90 Hz, 2H) 2.36 (s, 3H) 2.04 (s, 3H) 1.28 (t, J=7.14 Hz, 2H).

Aufarbeitung

  1. extractionIt was extracted with EtOAc
  2. washThe organic layer was washed with saturated sodium bicarbonate, HCl (1 N) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by ISCO FC with 0-40% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-051439636c694a1bbc79747fcbdb238f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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