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1068-90-2 - Diethyl acetamidomalonate, 98+% - Acetamidomalonic acid diethyl ester - A14048 - Alfa Aesar

A14048 Diethyl acetamidomalonate, 98+%

Codice CAS
1068-90-2
Sinonimi
Acetamidomalonic acid diethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
25g 16,80
100g 32,30
500g 131,00
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Diethyl acetamidomalonate, 98+%

MDL
MFCD00009146
EINECS
213-952-9

Proprietà chimiche

Formula
CH3CONHCH(CO2CH2CH3)2
Peso formula
217.22
Punto di fusione
96-99°
Punto di ebollizione
185°/20mm
Solubilità
Soluble in chloroform and methanol. Slightly soluble in water.

Applicazioni

Diethyl 2-Acetamidomalonate, is a versatile building block used for the synthesis of various pharmaceutical and biologically active compounds. It is an intermediate for the preparation of Novobiocin analogues as potential heat shock protein 90 inhibitors. It is also used as a important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals.

Note

Store in cool, dry place in tightly closed containers. Store away from oxidizing agent.

Letteratura

Sambasivarao Kotha; Kuldeep Singh. N-Alkylation of diethyl acetamidomalonate: synthesis of constrained amino acid derivatives by ring-closing metathesis. Tetrahedron Letters. 2004, 45(52), 9607-9610.

Paul Angell; Peter G. Blazecka; Mark Lovdahl; and Ji Zhang. Indium(III)-Catalyzed Addition of Diethyl Acetamidomalonate to Terminal Alkynes:? An Efficient Approach to β-Branched α-Amino Acids. J. Org. Chem. 2007, 72(17), 6606-6609.

Intermediate for synthesis of racemic amino acids, by reaction with an electrophile, e.g alkyl halide, followed by hydrolysis and decarboxylation. The reactivity can be reversed by conversion to the dehydro-derivative, which then undergoes nucleophilic attack with alkyllithiums, Grignards, malonate anion, etc.: Angew. Chem. Int. Ed., 21, 203 (1982):

Substituents can also be introduced by Michael addition to a wide variety of acceptors: Synth. Commun., 18, 367 (1988).

For use in a novel pyrrole synthesis, see 1,4-Dichloro-2-butyne, A13300.

Compare also Diethyl­ formamidomalonate, L01189.

Altri riferimenti

Beilstein
783883
Codice tariffe armonizzato
2924.19
TSCA
Yes
RTECS
OO0360000

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