Acetic Acid → 2-(Acetylamino)-2-[[3-methoxy-2-(phenylmethoxy)phenyl]methyl]-propanedioic acid, diethyl ester

HRID 260082

Reaktionsgleichung

Reaktionsgleichung von HRID 260082
[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].Cl[CH2:17][C:18]1[C:19]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:20]([O:24][CH3:25])[CH:21]=[CH:22][CH:23]=1.O.C(O)(=O)C>C(O)C>[C:1]([NH:4][C:5]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([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 176Acetic AcidHCID 962WaterHCID 14041Acetamidomalonic acid diethyl esterHCID 224024543-(Chloromethyl)-2-phenylmethoxyanisole

Produkt 1

HCID 1317181682-(Acetylamino)-2-[[3-methoxy-2-(phenylmethoxy)phenyl]methyl]-propanedioic acid, diethyl esterAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A quantity of 136.20 g (0.42 mole) of 21 wt. % sodium ethoxide-in-ethanol is added to a stirred solution of 90.14 g (0.415 mole) of diethyl acetamidomalonate (Aldrich) in 800 mL of absolute ethanol. A solution of the benzyl chloride derivative of Example 38 in 500 mL of absolute ethanol is added and the mixture is heated at reflux for 2 hours. The cooled mixture is poured into 4 L of ice and water containing 20.0 g of glacial acetic acid. The supernatant is decanted from the separated gum. The gum is dissolved in 2 L of ether, the solution dried (magnesium sulfate), and concentrated to ca 300 mL volume. Petroleum ether (100 mL) is added to precipitate 107.1 g (66.4% yield) of pure crystalline product; mp 94°-96° C.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 hours
  3. customThe supernatant is decanted from the separated gum
  4. dissolutionThe gum is dissolved in 2 L of ether
  5. dry with materialthe solution dried (magnesium sulfate)
  6. concentrationconcentrated to ca 300 mL volume

Quellen und Nachweise

ORD-Eintrag
ord-869603e2c00c40c4b2b7d0e1fd100115
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05525614

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