106447-44-3

Basic information

• Product Name: 7-AMINO-3-[(Z)-PROP-1-ENYL]-3-CEPHEM-4-CARBOXYLIC ACID
• Synonyms: 7-AMINO-3-[(Z)-PROP-1-ENYL]-3-CEPHEM-4-CARBOXYLIC ACID;3-(cis-1-propenyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-7-AMino-8-oxo-3-(1Z)-1-propen-1-yl-5--thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;Cefprozil Related CoMpound D;(6R,7R)-7-Amino-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefprozil Related Compound D (30 mg) ((6R,7R)-7-amino-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid);(6R,7R)-7-Amino-8-oxo-3-(1Z)-1-propen-1-yl-5--thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (>90%)
• CAS NO: 106447-44-3
• Molecular Formula: C₁₀H₁₂N₂O₃S
• Molecular Weight: 240.28
• EINECS: 415-750-8
• Product Categories: Aromatics, Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 106447-44-3.mol

Chemical Properties

• Boiling Point: 539.275°C at 760 mmHg
• Flash Point: 279.944°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Base (Slightly), DMSO (Sparingly, Heated, Sonicated)
• PKA: 2.84±0.50(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 7-AMINO-3-[(Z)-PROP-1-ENYL]-3-CEPHEM-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 7-AMINO-3-[(Z)-PROP-1-ENYL]-3-CEPHEM-4-CARBOXYLIC ACID(106447-44-3)
• EPA Substance Registry System: 7-AMINO-3-[(Z)-PROP-1-ENYL]-3-CEPHEM-4-CARBOXYLIC ACID(106447-44-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 22-24-37
• WGK Germany: 3
• Hazardous Substances Data: 106447-44-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-AMINO-3-[(Z)-PROP-1-ENYL]-3-CEPHEM-4-CARBOXYLIC ACID is used as an impurity in the production of Cefprozil, an oral cephalosporin antibiotic, for its role in the development and synthesis of the final antibiotic product. The presence of this compound in the production process is essential for the effectiveness of Cefprozil as an antibacterial agent.
As an impurity in the production of Cefprozil, 7-AMINO-3-[(Z)-PROP-1-ENYL]-3-CEPHEM-4-CARBOXYLIC ACID contributes to the overall efficacy of the antibiotic, which is used to treat various bacterial infections. The compound's presence in the synthesis process may also play a role in the formation of the Z/E isomeric mixture, which is characteristic of Cefprozil's composition.

InChI:InChI=1/C10H12N2O3S/c1-2-3-5-4-16-9-6(11)8(13)12(9)7(5)10(14)15/h2-3,6,9H,4,11H2,1H3,(H,14,15)/b3-2-

Upstream product

• 75-07-0 acetaldehyde 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 190790-85-3 (7R,8R)-7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester 

Downstream Products

• 121412-77-9 cefprozil 
• 110764-35-7 7-[D-α-amino-α-(4-hydroxyphenyl)acetamido]-3-(1-propen-1-yl)-3-cephem-4-carboxylic acid 

Relevant articles and documents

A refining method of Cefprozil (by machine translation)

The invention relates to a kind of Cefprozil refining method, including Cefprozil crude synthesis and Cefprozil refining, wherein the refining comprises: 1) will Cefprozil crude product in adding ethanol, stirring, dilute hydrochloric acid aqueous solution to adjust the pH to 2.0 - 2.2, stirring, dissolving crude product, filtering, to obtain the Cefprozil salt of the crude solution; 2) the above-mentioned solution adds by drops to 4% sodium bicarbonate solution, adjusting the pH to 4.6 - 5.0, cooling, thermal insulation mixing, filtering, washing, and a ground line, to get the solid; 3) step 2) the resulting solid dissolved in water, adding activated carbon, heating to 30 - 35 °C, fully stirring, after filtering the filtrate, the filtrate is cooled to 0 - 5 °C, added to the mixed solvent, crystallization, control the temperature and the stirring speed brilliantly 1.5 h, filtering, washing, and a ground line, vacuum drying, spore propylene pure product. The present invention provides a refined method has the simple conditions, cis-isomer content high, high purity and the like. (by machine translation)

Synthetic method of cefprozil

The invention relates to a synthetic method of cefprozil. The synthetic method comprises the following steps: iodination reaction and Wittig reaction are performed on 7-ACA as a starting material after silylation protection, and a compound 2 is generated; a compound 1, namely, the target product cefprozil is generated from the compound 2 and methyl D-(-)-4-hydroxy-phenylglycinate under catalysis of AlMe3. The conversion rate is high, the process is simple, the cis-isomer content is high, and the synthetic method is suitable for large-scale industrial production.

A 7 - amino - 3 - propylene - 1 - yl - 3 - cephem - 4 - carboxylic acid synthesizing method

The invention relates to a synthesis method of high-purity 7-amino-3-propylene-1-yl-3-cephem-4-carboxylic acid. The method takes deacetylated-7-aminocephalosporanic acid (D-7-ACA) as a starting raw material, and the starting raw material is reacted with ethyltriphenyl phosphonium bromide through oxidization to generate the 7-amino-3-propylene-1-yl-3-cephem-4-carboxylic acid. The synthesis method has a simple process, low cost and high product yield; the purity is more than 99% and the synthesis method is suitable for industrial production.

PROCESSES FOR THE PREPARATION OF CEPHEM DERIVATIVES

Provided is a process for preparing a compound of formula 1 or its salt, which includes reacting a compound of formula 2 with a compound of formula 3 in the presence of a base.

PROCESSES FOR THE PREPARATION OF CEPHALOSPORIN DERIVATIVES

Provided is a process for preparing a compound of formula 1 or its salt. The process includes reacting a compound of formula 4 with acetaldehyde in a mixed solvent including water, isopropanol, and methylenechloride in a volume ratio of 1:3-6:11-14 in the

PROCESS FOR THE PREPARATION OF (Z)-ISOMER ENRICHED 7-AMINO-3-PROPEN-1-YL-3-CEPHEM-4- CARBOXYLIC ACID

The invention relates to a process for enrichment of the (Z)-isomer amount in a mixture of the (Z)- and (E)- isomers of 7-amino-3-(1-propen-1-yl)-3-cephem-4-carboxylic acid.