aztreonam

Base Information

• Chemical Name: aztreonam
• CAS No.: 80951-91-3
• Molecular Formula: C₁₃H₁₇N₅O₈S₂
• Molecular Weight: 435.439
• Mol file: 80951-91-3.mol

Synonyms:Propanoic acid, 2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methyl-, [2R-[2α,3α(Z)]]- (9CI)

Chemical Property of aztreonam

Chemical Property:

• PKA: -0.24±0.60(Predicted)
• PSA: 242.42000
• Density: 1.83±0.1 g/cm3(Predicted)
• LogP: 0.61660

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of aztreonam

There total 36 articles about aztreonam 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: 86.9%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester (89604-92-2,158183-05-2) → azthreonam (78110-38-0,80951-91-3,149496-40-2,99341-02-3,85506-30-5)

Guidance literature:

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid; (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester; With pyridine; In acetonitrile; at -5 ℃; for 4h;

With nitric acid; at 35 ℃; for 2h; pH=1; Solvent; Reagent/catalyst; Temperature;

Reference yield: 81.0%

(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt (139714-28-6) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → azthreonam (78110-38-0,80951-91-3,149496-40-2,99341-02-3,85506-30-5)

Guidance literature:

(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid; With triethylamine; In ethanol; water; at -6 - -3 ℃; for 3h;

With hydrogenchloride; In ethanol; water; at -3 - 0 ℃;

DOI:10.1021/op025572d

Reference yield: 72.0%

[3S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid (330944-50-8) → azthreonam (78110-38-0,80951-91-3,149496-40-2,99341-02-3,85506-30-5)

Guidance literature:

With hydrogenchloride; water; at 0 - 65 ℃; for 4.75h;

upstream raw materials:

3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid

[3S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid

aztreonam

water

Downstream raw materials:

aztreonam

Refernces

• 1、 Ding, Pingyu,Duncton, Matthew A. J.,Fan, Dazhong,Gordon, Eric M.,Grygorash, Ruslan,Li, Xianfeng,Low, Eddy,Ni, Zhi-Jie,Qi, Longwu,Sun, Jiawei,Wang, Brian J.,Yu, Guijun. "Toward Orally Absorbed Prodrugs of the Antibiotic Aztreonam. Design of Novel Prodrugs of Sulfate Containing Drugs. Part 2". . p. 162 - 165. Retrieved 2020/01/31.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF MONOBACTAM ANTIBIOTIC". Page/Page column 8-9. . Retrieved 2008/06/13.