(6S,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (6S,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 68401-81-0
• Molecular Formula: C13H13N5O5S2
• Molecular Weight: 383.409
• Hs Code.: 2941906000
• European Community (EC) Number: 685-309-4
• Wikipedia: Ceftizoxime
• Mol file: 68401-81-0.mol

Synonyms:68401-81-0;SCHEMBL9367024;AKOS025402139;AC-5543

Chemical Property of (6S,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white or light ashy-yellow crystalline powder
• Melting Point: 227° (dec)
• PKA: pKa 2.1 (Uncertain)
• PSA: 200.75000
• Density: 1.89 g/cm³
• LogP: 0.35420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated, So
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 383.03581088
• Heavy Atom Count: 25
• Complexity: 669

Purity/Quality:

99% ^*data from raw suppliers

Ceftizoxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=CCS3)C(=O)O
• Isomeric SMILES: CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@H]3N(C2=O)C(=CCS3)C(=O)O
• Description: In ceftizoxime, the whole C-3 side chain has been omitted to prevent deactivation by hydrolysis. It rather resembles cefotaxime in its properties; however, not being subject to metabolism, its pharmacokinetic properties are much less complex.
• Uses: Antibacterial. Ceftizoxime is used for bacterial infections of the lower respiratory tract, infections of the urinary tract, infections of the bones, joints, skin, soft tissues, and abdominal infections. Synonyms of this drug are ceftix and eposerin. Ceftizoxime is a cephalosporin based, potent antibacterial agent.
• Therapeutic Function: Antibacterial

Technology Process of (6S,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 9 articles about (6S,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 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: 97.0%

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + C13H10N4O2S3 → ceftizoxime (68401-81-0)

Guidance literature:

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With dmap; In dichloromethane; at -8 - 0 ℃;

C₁₃H₁₀N₄O₂S₃; With dmap; In dichloromethane; at -5 - 0 ℃; for 0.25h; Reagent/catalyst; Temperature;

Reference yield: 91.0%

ceftizoximate diphenylmethyl ester → (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-ceph-3-em-4-carboxylic acid (68401-81-0,68403-31-6,74708-63-7)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; at 30 ℃; for 3h; Solvent; Temperature; Reagent/catalyst;

Reference yield:

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) → ceftizoxime (68401-81-0)

Guidance literature:

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; With triethylamine; In chloroform; for 0.333333h;

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; In chloroform; at 35 ℃; for 4.5h; Temperature;

upstream raw materials:

7β-amino-ceph-3-em-4-carboxylic acid diphenylmethyl ester

2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid

pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

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

Downstream raw materials:

(6R,7R)-7-{2-[2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-cyclohexyloxycarbonyloxy-ethyl ester

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-cyclohexyloxycarbonyloxy-ethyl ester

Refernces

• 1、 -. "A one-head spore zuozuo wo sodium compound (by machine translation)". Paragraph 0027; 0028; 0034. . Retrieved 2019/01/17.
• 2、 -. "NOVEL INTERMEDIATES FOR SYNTHESIS OF CEPHALOSPORINS AND PROCESS FOR PREPARATION OF SUCH INTERMEDIATES". Page 33. . Retrieved 2008/06/13.