Triethylamine → Butanoic acid, 2-[(cyclohexylcarbonyl)amino]-3-oxo-, ethyl ester

HRID 1440230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1440230
Cl.[NH2:2][CH:3]([C:9]([CH3:11])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:12]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:12]1([C:18]([NH:2][CH:3]([C:9]([CH3:11])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 13282897Ethyl 2-amino-3-oxobutanoate hydrochloride

Produkt 1

HCID 12282192Butanoic acid, 2-[(cyclohexylcarbonyl)amino]-3-oxo-, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 23.6 g of ethyl alpha-aminoacetoacetate hydrochloride in 450 ml of chloroform cooled to 0° C. was added 19.52 ml of cyclohexylcarbonyl chloride. After 20 minutes at 0° C. 36 ml of triethylamine was added dropwise over a period of 30 minutes. The reaction mixture was allowed to warm to room temperature, was washed with water (2×300 ml) and brine (300 ml) and dried over magnesium sulfate. Removal of the solvent in vacuo gave 35.1 g of an oil which on chromatographing on 400 g of silica gel (hexane-ethyl acetate; 7.5:2.5; v:v) gave 13.9 g of product, m.p. 74°-75° C.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. washwas washed with water (2×300 ml) and brine (300 ml)
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d5e2d064ec384e5fb92dc97103e34206
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498621

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