55327-87-2

Basic information

• Product Name: Acetamidomalonic acid
• Synonyms: Acetamidomalonic acid
• CAS NO: 55327-87-2
• Molecular Formula: C₅H₇NO₅
• Molecular Weight: 161.11278
• Mol File: 55327-87-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acetamidomalonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamidomalonic acid(55327-87-2)
• EPA Substance Registry System: Acetamidomalonic acid(55327-87-2)

Safety Data

• Hazardous Substances Data: 55327-87-2(Hazardous Substances Data)

Upstream product

• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 60187-67-9 dimethyl acetamidomalonate 
• 51887-51-5 dibenzyl acetamidomalonate 
• 1068-84-4 2-aminomalonic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 89131-42-0 3-amino-3-carboxypropylphosphonous acid 
• 1254841-05-8 (S,Z)-2-acetamido-5-(2,3-difluorophenyl)-6-nitrohex-2-enoic acid 

Relevant articles and documents

Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system

(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.

Synthesis and decarboxylation of Δ2-cephem-4,4-dicarboxylic acids

Penicillin V was converted in 14 steps into Δ2-cephems having hydrogen at C-3, hydrogen or methyl at C-2, and two methoxycarbonyl, two benzyloxycarbonyl, or one methoxycarbonyl and one benzyloxycarbonyl substituent at C-4. Deprotection of these Δ2-cephem-4,4-dicarboxylic acid esters by alkaline hydrolysis (in the case of methyl esters) or hydrogenolysis (in the case of benzyl esters) led in all cases to rapid decarboxylation of the Δ2-cephem-4,4-dicarboxylic acid or Δ2-cephem-4,4-dicarboxylic acid monoester. With hydrogen at C-2, hydrolysis of the dimethyl ester with 1 equiv of base produced a Δ2-cephem. With 2 equiv of base, and with all compounds having methyl at C-2, hydrolysis or hydrogenolysis afforded 4α-substituted-Δ2-cephems. In contrast, simpler benzyl or methyl acetamidomalonates could be deprotected without difficulty to afford stable malonic acids. Reasons for the differences in ease of decarboxylation were examined using semiempirical (AM1) and ab initio (3-21G) molecular orbital calculations. The decarboxylation barriers of unionized cephem or acetamido malonic acids were found to be high (35-40 kcal mol-1). Although the monoanion of acetamidomalonic acid retained a high barrier, the epimeric monoanions of a Δ2-cephem malonic acid decarboxylated with barriers of only 2 kcal mol-1.