Acetamidomalonic acid diethyl ester → Diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonate

HRID 1828332

Reaktionsgleichung

Reaktionsgleichung von HRID 1828332
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[C:20]=1[CH2:21]Br>C(O)C.O1CCCC1>[C:2]([NH:5][C:6]([CH2:21][C:20]1[C:23]([N+:27]([O-:29])=[O:28])=[CH:24][CH:25]=[CH:26][C:19]=1[O:18][CH3:17])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

Komponenten

6

Edukt 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 186047Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-HCID 5360545Sodium

Produkt 1

HCID 21974615Diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonateAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium metal (1.15 g) was dissolved in absolute ethanol (500 mL), and to the resulting solution was added diethyl 2-acetylaminomalonate (9.1 g). After 15 min at room temperature, a solution of 2-methoxy-6-nitrobenzyl bromide (J. Med. Chem. 1977, 20, 190–196) (8.6 g) in tetrahydrofuran (25 mL) was added over 2 min. After 16 h stirring at room temperature the mixture was evaporated. The residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated and washed sequentially with water and brine before drying over anhydrous sodium sulfate. Evaporation was followed by silica gel chromatography eluting initially with dichloromethane, followed by ethyl acetate, to obtain diethyl 2-acetylamino-2-(2-methoxy-6-nitrobenzyl)malonate (10.8 g).

Aufarbeitung

  1. customwas evaporated
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed sequentially with water and brine
  5. dry with materialbefore drying over anhydrous sodium sulfate
  6. customEvaporation
  7. washeluting initially with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-cdf686f2fa4b4b22bee718b4821bab64
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07057046B2

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