(6R,7R)-7-azaniumyl-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: (6R,7R)-7-azaniumyl-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 22252-43-3
• Molecular Formula: C₈H₁₀N₂O₃S
• Molecular Weight: 214.245
• Hs Code.: 2941.90
• Mol file: 22252-43-3.mol

Synonyms:

Chemical Property of (6R,7R)-7-azaniumyl-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 4.18E-12mmHg at 25°C
• Melting Point: 234°C (dec.)
• Refractive Index: 104 ° (C=1, 1mol/L HCl)
• Boiling Point: 517.6 °C at 760 mmHg
• PKA: 3.04±0.50(Predicted)
• Flash Point: 266.8 °C
• PSA: 108.93000
• Density: 1.59 g/cm³
• LogP: 0.22560
• Storage Temp.: 2-8°C
• Solubility.: Do you have solubility information on this product that you woul
• Water Solubility.: Soluble in water (partly), 1M ammonium hydroxide (50 mg/ml), and DMSO (Sparingly).
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 214.04121336
• Heavy Atom Count: 14
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

7-Aminodesacetoxycephalosporanic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43-36/37/38-20/21/22
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N2C(C(C2=O)[NH3+])SC1)C(=O)[O-]
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)[NH3+])SC1)C(=O)[O-]
• Uses: A metabolite of Cephalexin (C256800). 7-Aminodesacetoxycephalosporanic acid is the Cephalexin metabolite. It is a Potent inhibitor of bacterial cell-wall enzyme. It is used in the synthesis of cephalosporins and for bioconversion studies.

Technology Process of (6R,7R)-7-azaniumyl-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 30 articles about (6R,7R)-7-azaniumyl-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 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: 100.0%

(6R,7R)-7-Amino-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-methyl-but-2-enyl ester → 3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9)

Guidance literature:

With diethylamine; Pd⁽⁰⁾ (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine); In water; acetonitrile; for 1h; 5 molpercent catalyst;

DOI:10.1016/S0040-4039(00)78497-8

Reference yield: 48.0%

→ 3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) + pyridine-4-carboxylic acid (55-22-1)

Guidance literature:

Reference yield:

(6R,7R)-7-Allyloxycarbonylamino-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-methyl-but-2-enyl ester → 3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / diethylamine / Pd⁽⁰⁾ (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / acetonitrile; H₂O / 0.5 h / 2.5 molpercent catalyst

2: 100 percent / diethylamine / Pd⁽⁰⁾ (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / acetonitrile; H₂O / 1 h / 5 molpercent catalyst

With diethylamine; Pd⁽⁰⁾ (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine); In water; acetonitrile;

DOI:10.1016/S0040-4039(00)78497-8

upstream raw materials:

(6R)-3-methyl-8-oxo-7t-(2,2,2-trifluoro-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-3-methyl-8-oxo-7t-(trimethylsilanyl-amino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid trimethylsilanyl ester

acetoxymethyl 7β-phenylacetamido-3-methyl-3-cephem-4-carboxylate

acetoxymethyl 7-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate

Downstream raw materials:

(6R)-7t-amino-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Deacetoxy-7-(D-α-1'-Cyclohexenylglycinamido)-cephalosporansaeure

(6R)-7t-[(Ξ)-2-acetoxy-2-(4-chloro-phenyl)-acetylamino]-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-7t-[(Ξ)-2-acetoxy-2-(4-bromo-phenyl)-acetylamino]-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 STEDMAN,SWERED,HOOVER. "7-AMINODESACETOXYCEPHALOSPORANIC ACID AND ITS DERIVATIVES.". . p. 117 - 119. Retrieved 1964.
• 2、 Blum, Janna K.,Bommarius, Andreas S.. "Amino ester hydrolase from Xanthomonas campestris pv. campestris, ATCC 33913 for enzymatic synthesis of ampicillin". scheme or table. p. 21 - 28. Retrieved 2010/12/19.