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
• Article Data: 6

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

(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 is an impurity of Cefprozil (C243910), an semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture and is an antibacterial agent.

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

• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 75-07-0 acetaldehyde 
• 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)

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 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