18715-92-9

Basic information

• Product Name: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(4R)-2,2-dimethyl-5-oxo-4-phenyl- 1-imidazolidinyl]-3,3-dimethyl-7-oxo-,(2S,- 5R,6S)-
• Synonyms: 6-Epihetacillin;(2S,5R,6S)-6-((R)-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;epihetacillin;6-Epi-hetacillin;Epiketacillin
• CAS NO: 18715-92-9
• Molecular Formula: C19H23N3O4S
• Molecular Weight: 389.475
• Mol File: 18715-92-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(4R)-2,2-dimethyl-5-oxo-4-phenyl- 1-imidazolidinyl]-3,3-dimethyl-7-oxo-,(2S,- 5R,6S)- (CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(4R)-2,2-dimethyl-5-oxo-4-phenyl- 1-imidazolidinyl]-3,3-dimethyl-7-oxo-,(2S,- 5R,6S)- (18715-92-9)
• EPA Substance Registry System: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(4R)-2,2-dimethyl-5-oxo-4-phenyl- 1-imidazolidinyl]-3,3-dimethyl-7-oxo-,(2S,- 5R,6S)- (18715-92-9)

Safety Data

• Hazardous Substances Data: 18715-92-9(Hazardous Substances Data)

Upstream product

• 40439-01-8 hetacillin 
• 3511-16-8 hetacillin 
• 5321-32-4 hetacillin potassium 

Downstream Products

• 217644-25-2 (4S)-2t-((2S)-3,6-dioxo-5c-phenyl-piperazin-2r-yl)-5,5-dimethyl-thiazolidine-4r-carboxylic acid 
• 49841-95-4 6α-((R)-2-amino-2-phenyl-acetylamino)-penicillanic acid 
• 65058-91-5 6α-((R)-2,2-dimethyl-3-nitroso-5-oxo-4-phenyl-imidazolidin-1-yl)-penicillanic acid 
• 69-53-4 6-epi-ampicillin 
• 22888-48-8 6β-((R)-2-benzylamino-2-phenyl-acetylamino)-penicillanic acid benzyl ester 
• 21794-95-6 6α-(2-phenyl-acetylamino)-penicillanic acid methyl ester 
• 47294-44-0 6α-(2-phenyl-acetylamino)-penicillanic acid 
• 49841-97-6 (4S)-2t-((2S)-3,6-dioxo-5c-phenyl-piperazin-2r-yl)-5,5-dimethyl-thiazolidine-4r-carboxylic acid methyl ester 
• 94595-14-9 2-(3,6-dioxo-5-phenylpiperazine-2-yl)-5,5-dimethylthiazolidine-4-carboxylic acid 
• 18715-93-0 6α-((R)-2,2-dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-penicillanic acid methyl ester 

Relevant articles and documents

Hydrolysis and epimerization kinetics of hetacillin in aqueous solution

Methods were developed for quantitating epimerization to epihetacillin and hydrolysis to ampicillin in the alkaline degradation of hetacillin, and both rates in deuterium oxide at 35° and in water at various temperatures were determined. In each case, plots of log k for the epimerization against pH or pD yielded straight lines with a positive slope, which verified the first-order dependence on the hydroxide ion or deuteroxide ion. The activation energy of the epimerization process was 21.2 kcal/mole. In aqueous solution at high pH, epimerization rather than conversion to ampicillin represents a major pathway of hetacillin degradation, although the β-lactam ring of the hetacillin molecule is highly resistant to attack by the hydroxide ion.

Preparation of 6-epi-ampicillin and of 6-epi-α-hydroxybenzylpenicillin

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