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120709-09-3

(6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, also known as 7-APCA, is a β-lactam compound that serves as a synthetic intermediate for the development of therapeutically useful β-lactam antibiotics. It is characterized by its unique molecular structure, which includes a β-lactam ring and a thiazole ring, making it a promising candidate for the creation of novel antibiotics.

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  • (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

    Cas No: 120709-09-3

  • USD $ 1.2-5.0 / Kiloliter

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  • 120709-09-3 Structure

  • Basic information

    1. Product Name: (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2. Synonyms: 7-apra;5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-8-OXO-3-(1-PROPENYL)-, (6R,7R)-;(6R,7R)-7-AMINO-8-OXO-3-(1-PROPENYL)-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID;(6 R,7 R)-7-AMIMO-8-OXO-3-(1-PROPENYL)-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID;Cefprozil intermediate;(6R,7R)-7-amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbo;IntermediateoftheCefprozil;(6R,7R)-7-AMINO-8-OXO-3-(1-PROPENYL)-5-THIA-1-AZABICYLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID
    3. CAS NO:120709-09-3
    4. Molecular Formula: C10H12N2O3S
    5. Molecular Weight: 240.28
    6. EINECS: 1312995-182-4
    7. Product Categories: N/A
    8. Mol File: 120709-09-3.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 539.275 °C at 760 mmHg
    3. Flash Point: 279.944 °C
    4. Appearance: /
    5. Density: 1.5 g/cm3
    6. Refractive Index: 1.685
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
    8. Solubility: Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonicated)
    9. PKA: 2.84±0.50(Predicted)
    10. CAS DataBase Reference: (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(CAS DataBase Reference)
    11. NIST Chemistry Reference: (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(120709-09-3)
    12. EPA Substance Registry System: (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(120709-09-3)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 120709-09-3(Hazardous Substances Data)

120709-09-3 Usage

Uses

Used in Pharmaceutical Industry:
7-APCA is used as a synthetic intermediate for the development of β-lactam antibiotics, which are a class of antibiotics that are effective against a wide range of bacterial infections. The compound's unique structure allows for the creation of new antibiotics with improved properties, such as enhanced potency, broader spectrum of activity, and reduced susceptibility to bacterial resistance.
Used in Research and Development:
7-APCA is also utilized in research and development for the study of β-lactam antibiotics and their mechanisms of action. This knowledge can be applied to the design and synthesis of new antibiotics, as well as the understanding of bacterial resistance to these drugs.
Used in Drug Delivery Systems:
Similar to gallotannin, 7-APCA can be incorporated into novel drug delivery systems to enhance its applications and efficacy against bacterial infections. Various organic and metallic nanoparticles can be employed as carriers for 7-APCA delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

Check Digit Verification of cas no

The CAS Registry Mumber 120709-09-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,0,7,0 and 9 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 120709-09:
(8*1)+(7*2)+(6*0)+(5*7)+(4*0)+(3*9)+(2*0)+(1*9)=93
93 % 10 = 3
So 120709-09-3 is a valid CAS Registry Number.
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)/t6-,9-/m1/s1

120709-09-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (6R,7R)-7-Amino-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

1.2 Other means of identification

Product number -
Other names (6R,7R)-7-Amino-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:120709-09-3 SDS

120709-09-3Synthetic route

acetaldehyde
75-07-0

acetaldehyde

7-Aminocephalosporanic acid
957-68-6

7-Aminocephalosporanic acid

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid
120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: 7-Aminocephalosporanic acid With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane In benzene for 2h; Inert atmosphere; Reflux;
Stage #2: With trimethylsilyl iodide In benzene at 0℃; for 1h;
Stage #3: acetaldehyde Reagent/catalyst; Further stages;		84.24%
(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid
120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

D-2-p-hydroxyphenylglycine methyl ester
37763-23-8

D-2-p-hydroxyphenylglycine methyl ester

7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-(propen-1-yl)-3-cephem-4-carboxylic acid
92665-29-7

7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-(propen-1-yl)-3-cephem-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid With penicillin acylase at 30 - 35℃; for 0.5h; pH=7; Enzymatic reaction;
Stage #2: D-2-p-hydroxyphenylglycine methyl ester With sodium lauryl sulfate In 1,4-dioxane at 30 - 35℃; for 2h; Reagent/catalyst;		97.74%
(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid
120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride

((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride

A

cefprozil
121412-77-9

cefprozil

B

E-cefprozil
92676-86-3

E-cefprozil

Conditions
ConditionsYield
Stage #1: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid; ((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride With triethylamine In dichloromethane; water at -40 - 0℃; for 3h;
Stage #2: With hydrogenchloride In dichloromethane; water for 1h;
Stage #3: With sodium hydroxide In dichloromethane; water at 0℃; for 2h; pH=3.2;
Stage #1: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid; ((R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetyloxy)-(triphenyl)phosphonium chloride With triethylamine In ISOPROPYLAMIDE; water at -40 - 0℃; for 3h;
Stage #2: With hydrogenchloride In ISOPROPYLAMIDE; water for 1h;
Stage #3: With sodium hydroxide In ISOPROPYLAMIDE; water at 0℃; for 2h; pH=3.2;
(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid
120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

A

cefprozil
121412-77-9

cefprozil

B

E-cefprozil
92676-86-3

E-cefprozil

Conditions
ConditionsYield
Stage #1: potassium (R)-(2-ethoxycarbonyl-1-methyl-vinylamino)-(4-hydroxyphenyl)-acetate With pyridine; pivaloyl chloride In DMF (N,N-dimethyl-formamide); dichloromethane at -30℃; for 2h;
Stage #2: (7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid With triethylamine In DMF (N,N-dimethyl-formamide); dichloromethane; water at -40 - 0℃; for 3h;
(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid
120709-09-3

(6R,7R)-7-amino-3-(propen-1-yl)-3-cephem-4-carboxylic acid

C12H17NO5

C12H17NO5

C22H27N3O7S

C22H27N3O7S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;

120709-09-3Relevant articles and documents

Preparation method of cefprozil

-

Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0032-0035, (2019/04/14)

The invention relates to a preparation method of cefprozil. A synthesis method comprises the following steps: taking 7-ACA (7-aminocephalosporanic acid) as a starting raw material; after carrying outsilylation protection, carrying out a series of reactions including iodination and the like to generate a compound 2; taking the compound 2 to react with methyl D-(-)-4-hydroxy-phenylglycinate under the catalysis of immobilized penicillin acylase to generate a compound 1, so as to obtain a target product cefprozil. The preparation method provided by the invention has the advantages of moderate reaction conditions, environmental friendliness, high conversion ratio, simple technology and high cis-isomer content.

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