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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.
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.
Hazard Statements: H302-H315-H319-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant