Hydrochloric Acid → Diethyl 2-acetamido-2-docosylmalonate

HRID 617827

Reaktionsgleichung

Reaktionsgleichung von HRID 617827
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[O-]CC.[Na+].[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].Cl>C(O)C>[C:1]([NH:4][C:5]([CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14041Acetamidomalonic acid diethyl esterHCID 813551-BromodocosaneHCID 2723922Sodium ethoxide

Produkt 1

HCID 21849362Diethyl 2-acetamido-2-docosylmalonateAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.5 g of docosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1 N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4.2 g of diethyl 2-acetamido-2-docosylmalonate.

Aufarbeitung

  1. temperaturethe mixture was refluxed for about 15 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4418efd7bff54d348a7758b0afcb391b
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952316

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