7-Amino-8-oxo-3-((1Z)-prop-1-enyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)-

Base Information

• Chemical Name: 7-Amino-8-oxo-3-((1Z)-prop-1-enyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)-
• CAS No.: 106447-44-3
• Molecular Formula: C10H12 N2 O3 S
• Molecular Weight: 240.283
• Hs Code.: 2941906000
• European Community (EC) Number: 415-750-8
• UNII: N023N3832V
• Wikidata: Q27284325
• Mol file: 106447-44-3.mol

Synonyms:106447-44-3;N023N3832V;7-Amino-8-oxo-3-((1Z)-prop-1-enyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)-;(6R,7R)-7-Amino-8-oxo-3-((Z)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-amino-8-oxo-3-(1Z)-1-propen-1-yl-, (6R,7R)-;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-amino-8-oxo-3-(1Z)-1-propenyl-, (6R,7R)-;7-APRA;Cefprozil impurity D [EP];UNII-N023N3832V;Cefprozil specified impurity D [EP];Cefprozil monohydrate impurity D [EP];7-APCA;EC 415-750-8;SCHEMBL10711330;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 (>90%);5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-amino-8-oxo-3-(1-propenyl)-, (6R-(3(Z),6alpha,7beta))-;CEFPROZIL IMPURITY D [EP IMPURITY];CEFPROZIL MONOHYDRATE IMPURITY D [EP IMPURITY];Q27284325;(6R,7R)-7-amino-8-oxo-3-((1Z)-prop-1-enyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;(6R,7R)-7-Amino-8-oxo-3-((Z)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;(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;(6R,7R)-7-AMINO-8-OXO-3-[(1Z)-PROP-1-EN-1-YL]-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID;5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-8-OXO-3-(1-PROPENYL)-, (6R-(3(Z),6.ALPHA.,7.BETA.))-

Chemical Property of 7-Amino-8-oxo-3-((1Z)-prop-1-enyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.685
• Boiling Point: 539.275°C at 760 mmHg
• PKA: 2.84±0.50(Predicted)
• Flash Point: 279.944°C
• PSA: 108.93000
• Density: 1.5g/cm³
• LogP: 0.78180
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Sparingly, Heated, Sonicated)
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 240.05686342
• Heavy Atom Count: 16
• Complexity: 416

Purity/Quality:

99.9% ^*data from raw suppliers

(6R,7R)-7-Amino-8-oxo-3-(1Z)-1-propen-1-yl-5--thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicAcid(>90%) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 22-24-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=C(N2C(C(C2=O)N)SC1)C(=O)O
• Isomeric SMILES: C/C=C\C1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O
• 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.

Technology Process of 7-Amino-8-oxo-3-((1Z)-prop-1-enyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)-

There total 4 articles about 7-Amino-8-oxo-3-((1Z)-prop-1-enyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, (6R,7R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.34%

C32H39N2O3PSSi2 + acetaldehyde (75-07-0,9002-91-9) → cis-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid (106447-44-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; at 20 ℃; for 1.5h;

Reference yield: 84.8%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + C8H8N2O4S → cis-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid (106447-44-3) + trans-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid (107937-01-9)

Guidance literature:

N,O-bis-(trimethylsilyl)-acetamide; C₈H₈N₂O₄S; In dichloromethane; at 20 ℃; for 3h;

With ethyltriphenylphosphonium bromide; In dichloromethane; at 0 - 5 ℃; for 3h; Temperature;

Reference yield:

(7R,8R)-7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester (190790-85-3) → cis-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid (106447-44-3) + trans-7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid (107937-01-9)

Guidance literature:

With pyridine; phosphorus pentachloride; In dichloromethane; at 20 ℃; for 0.5h;

(7R,8R)-7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester; In dichloromethane; for 2h;

With propylene glycol; water; ortho-cresol; more than 3 stages;

upstream raw materials:

(7R,8R)-7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester

N,O-bis-(trimethylsilyl)-acetamide

acetaldehyde

Downstream raw materials:

cefprozil

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

Refernces

• 1、 -. "Synthetic method of cefprozil". Paragraph 0020; 0029; 0031; 0033; 0039; 0045; 0051. . Retrieved 2018/05/30.
• 2、 -. "PROCESSES FOR THE PREPARATION OF CEPHEM DERIVATIVES". Page/Page column 18. . Retrieved 2008/06/13.