33993-48-5

Basic information

• Product Name: DL-Ampicillin
• Synonyms: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo- (6CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-;anhydrous ampicillin;DL-Ampicillin;DL-α-Aminobenzylpenicillin;(2S,5R,6R)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS NO: 33993-48-5
• Molecular Formula: C₁₆H₁₉N₃O₄S
• Molecular Weight: 349.40476
• Mol File: 33993-48-5.mol

Chemical Properties

• Melting Point: 205 °C
• Boiling Point: 683.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• PKA: 2.44±0.50(Predicted)
• CAS DataBase Reference: DL-Ampicillin(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Ampicillin(33993-48-5)
• EPA Substance Registry System: DL-Ampicillin(33993-48-5)

Safety Data

• Hazardous Substances Data: 33993-48-5(Hazardous Substances Data)

Upstream product

• 37661-08-8 bacampicillin hydrochloride 
• 1256-08-2 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 17191-31-0 N-[(4-methoxy-2-nitro-phenylsulfanylamino)-phenyl-acetoxy]-succinimide 
• 3511-16-8 6-epi-hetacillin 
• 40439-01-8 hetacillin 
• 551-16-6 6-Aminopenicillanic Acid 
• 6591-61-3 D-(-)-α-aminophenylacetic acid methyl ester 
• 65587-54-4 2',2'-Dibrompropoxycarbonyl-ampicillin-ONa 
• 17303-44-5 6β-[(Ξ)-2-(4-methoxy-2-nitro-phenylsulfanylamino)-2-phenyl-acetylamino]-penicillanic acid 

Downstream Products

• 38087-61-5 6β-((Ξ)-2-acetylamino-2-phenyl-acetylamino)-penicillanic acid 
• 38087-62-6 6β-[(Ξ)-2-(2-chloro-acetylamino)-2-phenyl-acetylamino]-penicillanic acid 
• 47749-89-3 6β-[(Ξ)-2-(2-phenoxy-acetylamino)-2-phenyl-acetylamino]-penicillanic acid 
• 26785-17-1 (2S,5R,6R)-6-(2-{[1-Furan-2-yl-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 90687-01-7 sodium salt of 6--2,2-dimethylpenam-3-carboxylic acid 
• 1256-08-2 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 143667-42-9 (2S,5R,6R)-3,3-Dimethyl-6-(2-{2-[(3-methyl-benzoyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 143667-43-0 (2S,5R,6R)-6-(2-{2-[(2-Hydroxy-benzoyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 139397-52-7 (2S,5R,6R)-6-(2-{2-[(2-Methoxy-benzoyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 143667-45-2 (2S,5R,6R)-3,3-Dimethyl-6-(2-{2-[(4-methylamino-benzoyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 143667-50-9 (2S,5R,6R)-6-(2-{2-[(4-Cyano-benzoyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 139491-97-7 (2S,5R,6R)-6-(2-{2-[(4-Methoxy-benzoyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 139397-55-0 (2S,5R,6R)-6-(2-{2-[(2,5-Dichloro-benzoyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 139397-59-4 (2S,5R,6R)-6-(2-{2-[(Biphenyl-4-carbonyl)-hydrazono]-acetylamino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 

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.

Extremely Selective and Mild Cleavage of β-Haloalkyl Groups by Cobalt(I)phthalocyanine Anion in Semisyntheses of β-Lactam Antibiotics

Cleavage of β-haloalkyl groups can be performed extremely selectively by cobalt(I)phthalocyanine anion under very mild conditions, qualifying it best in the chemistry of highly sensitive β-lactam antibiotics.This is demonstrated in penicillin and cephalosporin semisyntheses.