40439-01-8

Basic information

• Product Name: hetacillin
• Synonyms: hetacillin
• CAS NO: 40439-01-8
• Molecular Weight: 389.475
• Mol File: 40439-01-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: hetacillin(CAS DataBase Reference)
• NIST Chemistry Reference: hetacillin(40439-01-8)
• EPA Substance Registry System: hetacillin(40439-01-8)

Safety Data

• Hazardous Substances Data: 40439-01-8(Hazardous Substances Data)

Upstream product

• 33993-48-5 ampicillin 
• 67-64-1 acetone 

Downstream Products

• 110627-15-1 (2S,5R,6R)-6-(2,2-Dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyloxymethyl ester 
• 76890-96-5 (2S,5R,6R)-6-(2,2-Dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-methoxy-ethoxymethyl ester 
• 110637-10-0 (2S,5R,6R)-6-(2,2-Dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tetrahydro-furan-2-ylmethoxymethyl ester 
• 110637-12-2 (2S,5R,6R)-6-(2,2-Dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid tetrahydro-pyran-2-ylmethoxymethyl ester 
• 3511-16-8 6-epi-hetacillin 
• 69-53-4 6-epi-ampicillin 
• 94595-14-9 2-(3,6-dioxo-5-phenylpiperazine-2-yl)-5,5-dimethylthiazolidine-4-carboxylic acid 
• 110637-13-3 (2S,5R,6R)-6-(2,2-Dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-oxo-[1,3]dioxolan-4-ylmethyl ester 

Relevant articles and documents

Chemical reactivity of penicillins and cephalosporins. Intramolecular involvement of the acyl-amido side chain

The rate of degradation of 6-epi-ampicillin in acidic, neutral, and alkaline aqueous solutions was followed at 35 °C and an ionic strength of 0.5 mol dm-3 (KCl) by high-performance liquid chromatography (HPLC) and spectrophotometric assays. Pseudo-first-order rate constants were determined in a variety of buffer solutions, and the overall pH-rate profile was obtained by extrapolation to zero buffer concentration. The hydrolysis of 6- epi-ampicillin is subject to acid and hydroxide-ion catalysis and, for a penicillin, an unusual pH-independent reaction. Intramolecular general base- catalyzed hydrolysis by the side chain amido group is proposed to explain the enhanced rate of neutral hydrolysis of 6-epi-ampicillin and cephalosporins. The β-lactam of 6-epi-ampicillin also undergoes intramolecular aminolysis by nucleophilic attack of the 6-α side chain amino group to give a stable piperazine-2,5-dione derivative. The low effective molarity for intramolecular aminolysis of only 40 M is partly attributed to the unfavorable trans to cis isomerization about the 6-amide side chain required for ring closure. Theoretical calculations show that the intramolecular aminolysis of 6-epi-ampicillin nucleophilic attack occurs from the α-face of the β-lactam ring with an activation energy of 14.4 kcal/mol.

Methoxymethyl D-6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanate

The specification discloses a process for preparing methoxymethyl D-6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillanate and the use of this compound as a well absorbed antibacterial agent and also as an intermediate in the preparation of other antibiotic derivatives of 6-aminopenicillanic acid such as hetacillin. The methoxymethyl ester of ampicillin is also disclosed.