103121-85-3

Basic information

• Product Name: CefepiMe interMediate (7-PIME)
• Synonyms: CefepiMe interMediate (7-PIME);1-[[(6R,7R)-7-AMino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]Methyl]-1-MethylpyrrolidiniuM Chloride;CefepiMe Related CoMpound E;Cefepime Related Compound E (20 mg) (1-{[(6R,7R)-7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium chloride);Cefepime EP Impurity E
• CAS NO: 103121-85-3
• Molecular Formula: C13H20ClN3O3S
• Molecular Weight: 333.8342
• Product Categories: Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 103121-85-3.mol

Chemical Properties

• Boiling Point: 681℃[at 101 325 Pa]
• Appearance: /
• Density: 1.61[at 20℃]
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
• Water Solubility: 111g/L at 20℃
• Stability: Very Hygroscopic
• CAS DataBase Reference: CefepiMe interMediate (7-PIME)(CAS DataBase Reference)
• NIST Chemistry Reference: CefepiMe interMediate (7-PIME)(103121-85-3)
• EPA Substance Registry System: CefepiMe interMediate (7-PIME)(103121-85-3)

Safety Data

• Hazardous Substances Data: 103121-85-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CefepiMe interMediate (7-PIME) is used as a key intermediate in the synthesis of Cefepime, a fourth-generation cephalosporin antibiotic. It is utilized for its ability to contribute to the development of a potent and effective antibiotic that can combat a wide range of bacterial infections.
As an impurity in the synthesis of Cefepime, 7-PIME is also important for quality control and ensuring the safety and efficacy of the final antibiotic product. The presence of this impurity can impact the overall performance and safety profile of Cefepime, making it a critical factor to monitor and control during the manufacturing process.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C13H19N3O3S.ClH/c1-16(4-2-3-5-16)6-8-7-20-12-9(14)11(17)15(12)10(8)13(18)19;/h9,12H,2-7,14H2,1H3;1H/t9-,12-;/m1./s1

Upstream product

• 120-94-5 1-Methylpyrrolidine 
• 31461-04-8 3-acetoxy-7-trimethylsilylamino-3-cephem-4-carboxylic acid trimethylsilyl ester 
• 106134-67-2 (6R,7R)-trimethylsilyl 7-(trimethylsilyl)amino-3-iodomethylceph-3-em-4-carboxylate 
• 104146-10-3 (6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 

Downstream Products

• 107648-78-2 cefepime sulfate 
• 107648-80-6 1-[[(6R,7R)-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methyl-pyrrolidinium chloride hydrochloride 

Relevant articles and documents

Method for synthesizing cefepime hydrochloride intermediate

The invention provides a method for synthesizing a novel cefepime hydrochloride intermediate. The method comprises the following steps: with GCLE as a raw material, cutting off a position 4 protectinggroup (a p-methoxybenzyl group); then carrying out a reaction with N-methylpyrrolidine (NMP); and cutting off a position 7 protecting group by using an enzymatic process so as to obtain the intermediate 7-amino-3-(1-methyltetrahydropyrrole)methyl)-3-cephem-4-carboxylic acid hydrochloride (7-ACP). With the method, the prepared cefepime hydrochloride intermediate has high yield, high quality and nodelta2 isomers. The synthesis method has the advantages of simple process, no harsh reaction conditions and the like, and is therefore suitable for industrial production.

PROCESS FOR PRODUCTION OF INTERMEDIATES FOR USE IN CEFALOSPORIN SYNTHESIS

The invention relates to a new process for the production of intermediates for the synthesis of cephalosporin of formula (I) wherein R1, R2 and R3, independently of one another, are aklyl, alkenyl, aryl, hydroxy(C1-6)alkyl, carbamoyl-(C1-6)alkyl, amino-(C1-6)alkyl, aclamino-(C1-6)alkyl or carboxy(C1-6)alkyl, or wherein R2 and R3 together with the adjacent nitrogen atom, form an alicyclic 5- to 8-membered heterocyclic ring, and R1 signifies alkyl, alkenyl or aryl. The process according to the invention is notable in that the formation of undesired by-products, especially Δ2-analogous compounds of formula (I), is greatly reduced.

Use of Bistrimethylsilylated Intermediates in the Preparation of Semisynthetic 7-Amino-3-substituted-cephems. Expedient Syntheses of a New 3-cephalosporin

Several "one-pot" methods for conversion of 7-ACA (6) to a variety of 7-amino-3-(ammoniomethyl)- or 7-amino-3-methyl>cephalosporin derivatives via bistrimethylsilylated intermediates are presented.For example, bistrimethylsilylation of 7-ACA (6) in 1,1,2-trichlorotrifluoroethane (Freon TF) using HMDS and 3 mol percent TMSI, followed by treatment with 1.15 equiv of TMSI and subsequent reactions with tertiary alicyclic or heteroaromatic amines or heteroaromatic thiols, led to the desired products in good yields.Alternatively, novel reaction of the bistrimethylsilylated derivative 15 with amine/TMSI adducts in Freon TF at 35 deg C provided an alternative approach to some 7-amino-3-(ammoniomethyl)cephalosporins.The solvent dependence of Δ3/Δ2 isomer ratios in quaternization reactions of 11 with N-methylpyrrolidine is presented.Hypotheses for the explanation of experimental results observed on reaction of 15 in Freon TF with amine/TMSI adducts are presented.Acylation of 17 (X = Cl, I) with 8 in aqueous THF provided 18 (BMY-28142) as its sulfate salt in overall yields of 18percent and 43percent, respectively, from 7-ACA (6).