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78110-38-0 Usage

Outline

Aztreonam is a novel kind ofβ-lactam antibiotics belonging to monobactams. In 1978 it was first discovered from the culture brot of New Jersey soil purple bacterium Chromobacterium violaceum, it has been obtained with synthesis method.
Mechanism
Aztreonam belongs to bacteria fungicides. It can quickly go through the outer membrane of Gram-negative aerobic bacteria wall, while it has a high affinity with the penicillin-binding protein 3 (PBP-3) . By acting on the PBP-3 and inhibiting synthesis of bacterial cell wall , it leads to cell lysis and death.
Aztreonam has a narrow antimicrobial spectrum, it only has antibacterial effect on aerobic gram-negative bacilli , such as E. coli, Klebsiella, Serratia spp, Proteus mirabilis, indole-positive Proteus, Citrobacter, influenza addicted blood coli, Pseudomonas aeruginosa and other Pseudomonas, some Enterobacter, Neisseria gonorrhoeae. The product is highly stable to β-lactamase produced by many bacteria .it is inactive in Gram-positive bacteria and anaerobic bacteria . Aztreonam compared with ceftazidime, gentamicin, it effect on aerogenes, and Enterobacter cloacae is higher than ceftazidime, but lower than gentamicin; the effect on Pseudomonas aeruginosa is lower than ceftazidime , and similar to gentamicin .

Extinguishing agent

Dry powder, foam, sand, carbon dioxide, water spray.

Chemical Properties

White Crystalline Powder

Chemical properties

white or colorless powder crystals, melting at 227 ℃ (decomposition). It is dissolved in dimethyl formamide, slightly soluble in methanol, very slightly soluble in ethanol, insoluble in toluene, chloroform or ethyl acetate.
Aztreonam disodium: C13 H15N5Na2O8 . Acute toxicity LD50 (mg/kg): 3300 intravenous injection in mice, 6600 in rats intraperitoneally.

Toxicity grading

Middle toxic

production method

Threonine for raw materials,chloride resulting from the chlorination forms an amide through ammonolysis, protect α-amino with benzyl chloroformate,esterifyβ-hydroxy with methanesulfonyl chloride , the amide group is sulfonated with sulfuric acid tetrabutylammonium , then it is cyclized to generate azetidine derivative in the potassium bicarbonate, then after hydrogen and Deprotection, produce 3-amino-2-methyl-4-oxo-1-sulfo-N oxetane.
Afetr dehydration amidation of side chains Azetidine derivative and thiazole derivatives obtained in the above, hydrolyse to deprotect and to obtain aztreonam.

indications

It is mainly used for the treatment of infections caused by susceptible strains which include the respiratory system, urinary, reproductive system infections (including acute gonorrhea), intra-abdominal infections, skin and soft tissue infections, before surgery preventing infections, other serious infections, such as sepsis.

Uses

antiserotonin

Category

Toxic substances

Storage Characteristics

Ventilated, low-temperature ,dry storeroom.

Precautions

1.contraindication: patients allergic to the products or having a history of allergy on lidocaine and other local anesthetics or having anaphylactic shock on other β-lactam drugs are banned.
2. caution following:
It does not exist cross-allergic reactions between aztreonam and penicillins, but people having allergy body and allergic to penicillins, cephalosporins should take caution.
renal dysfunction patients should take caution.
aztreonam does not have toxicity for liver , but the patients having impaired liver function should observe the dynamic changes. It has been reported that in patients with alcoholic cirrhosis , the total clearance of the products can be reduced by 20-25%.
pregnant and lactating women, infants and young children should use with caution.
3. The impact of drugs on clinical outcomes:
direct anti-human globulin test (Coombs test) can be positive.
there may be a temporary increase of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase (LDH) and serum creatinine values after medication among a few patients, part thromboplastin time (PTT) and prothrombin time (PT) may be extended.
adverse reactions are skin symptoms such as skin rashes, purpura, pruritus (approximately 2%); gastrointestinal symptoms such as diarrhea, nausea, vomiting, taste changes, jaundice, and drug-induced hepatitis (approximately 2%); local irritation such as thrombophlebitis. Injection site swelling (approximately 2.4%); there are other neurological symptoms, vaginitis, oral lesions, fatigue, dizziness, and bleeding.
4. Long-term medication should pay attention to monitoring of liver, kidney and hematopoietic system.
The above information is edited by the chemicalbook of Tian Ye.

Uses

The first totally synthetic monocyclic β-lactam antibiotic.

Uses

It is Mainly used for the infections caused by sensitive gram-negative bacteria , including pneumonia, pleurisy, abdominal infections, biliary tract infections, bone and joint infections, skin and soft tissue inflammation, especially for urinary tract infections, but also for sepsis. Because this product has good resistance to enzyme performance, therefore, when a microorganism is not sensitive to penicillins, cephalosporins, aminoglycosides and other drugs ,the product should often be effective.

Acute toxicity

Intraperitoneal-rat LD50: 2549 mg/kg; intraperitoneal-Mouse LD50: 2897 mg/kg.

Uses

Aztreonam is a synthetic β-lactam antibiotic of the monobactam class. It is effective against Gram-negative bacteria but inactive against Gram-positive bacteria. Its mechanism of action involves the inhibition of mucopeptide synthesis in the bacterial cell wall, thereby blocking peptidoglycan crosslinking. Aztreonam is resistant to hydrolysis by some β-lactamases, but is inactivated by extended-spectrum β-lactamases.

Flammability and hazard characteristics

Combustible; combustion produces toxic fumes of nitrogen oxides and sulfur oxides.

Brand name

Azactam (Bristol-Myers Squibb).

Uses

The first totally synthetic monocyclic ?lactam antibiotic

78110-38-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name aztreonam

1.2 Other means of identification

Product number -
Other names Azonam

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:78110-38-0 SDS

78110-38-0Synthetic route

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid
80082-65-1

(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
89604-92-2

(Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Stage #1: (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;
Stage #2: With nitric acid at 35℃; for 2h; pH=1; Solvent; Reagent/catalyst; Temperature;
86.9%
(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

(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
80082-65-1

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Stage #1: (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;
Stage #2: With hydrogenchloride In ethanol; water at -3 - 0℃;
81%
[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

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

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With hydrogenchloride; water at 0 - 65℃; for 4.75h;72%
With water; trifluoroacetic acid at 0 - 63℃; for 1 - 21.75h;63%
With hydrogenchloride In water at 60℃; for 5h;
3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid
123539-91-3

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

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid In dichloromethane
2-[1-(2-Amino-thiazol-4-yl)-2-(diphenoxy-phosphoryloxy)-2-oxo-eth-(Z)-ylideneaminooxy]-2-methyl-propionic acid benzhydryl ester

2-[1-(2-Amino-thiazol-4-yl)-2-(diphenoxy-phosphoryloxy)-2-oxo-eth-(Z)-ylideneaminooxy]-2-methyl-propionic acid benzhydryl ester

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O
2: trifluoroacetic acid, anisole / CH2Cl2
View Scheme
aztreonam

aztreonam

6,7-Dihydroxy-2,3-quinolinedicarboxylic anhydride

6,7-Dihydroxy-2,3-quinolinedicarboxylic anhydride

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide; acetonitrile
azthreonam dipotassium salt

azthreonam dipotassium salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With hydrogenchloride In methanol; water
With hydrogenchloride In methanol; water
water
7732-18-5

water

3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid
123539-91-3

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

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With trifluoroacetic acid In acetone-denatured alcohol; ethanol; dichloromethane; methoxybenzene
(Z)-2-Amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]-imino]-4-thiazoleacetic acid
80542-76-3

(Z)-2-Amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]-imino]-4-thiazoleacetic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 2 h / 30 °C
2.1: methoxybenzene / dichloromethane / 1 h / 0 - 3 °C
3.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
3.2: 10 °C / pH 1.3
View Scheme
Multi-step reaction with 3 steps
1.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / acetonitrile / 3 h / 20 - 24 °C
1.2: 15 h / 20 °C
2.1: methanesulfonic acid; methoxybenzene / dichloromethane / 5 h / 0 °C
3.1: triethylamine / ethanol; water / 3 h / -6 - -3 °C
3.2: -3 - 0 °C
View Scheme
(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid diphenylmethyl ester methanesulfonate (1:1) salt
139714-26-4

(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid diphenylmethyl ester methanesulfonate (1:1) salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methanesulfonic acid; methoxybenzene / dichloromethane / 5 h / 0 °C
2.1: triethylamine / ethanol; water / 3 h / -6 - -3 °C
2.2: -3 - 0 °C
View Scheme
2-{[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethylidene]amino]oxy}-2-methylpropionic acid benzhydryl ester

2-{[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethylidene]amino]oxy}-2-methylpropionic acid benzhydryl ester

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: methoxybenzene / dichloromethane / 1 h / 0 - 3 °C
2.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
2.2: 10 °C / pH 1.3
View Scheme
2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate
477528-80-6

2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid
80082-65-1

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Stage #1: 2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid With triethylamine In methanol; water at 0℃; pH=8 - 8.5;
Stage #2: With hydrogenchloride In methanol; water at 10℃; pH=1.3;
174.2 g
C16H22N4O7SSi*ClH

C16H22N4O7SSi*ClH

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / N,N-dimethyl-formamide; ethyl acetate / 0.02 h / 10 °C
1.2: 10 °C
2.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
2.2: 10 °C / pH 1.3
View Scheme
2-amino-α-[(1-carboxy-1-methylethoxy)imino]-4-thiazoleacetic acid

2-amino-α-[(1-carboxy-1-methylethoxy)imino]-4-thiazoleacetic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide / 0.25 h / 50 °C
1.2: 3 h / -5 - 5 °C
2.1: triethylamine / N,N-dimethyl-formamide; ethyl acetate / 0.02 h / 10 °C
2.2: 10 °C
3.1: triethylamine / water; methanol / 0 °C / pH 8 - 8.5
3.2: 10 °C / pH 1.3
View Scheme
3-(3-amino-2-methyl-4-oxo-azetidine-1-sulfonyloxy)-2,2-dimethylpropionic acid ethyl ester methanesulfonic acid salt

3-(3-amino-2-methyl-4-oxo-azetidine-1-sulfonyloxy)-2,2-dimethylpropionic acid ethyl ester methanesulfonic acid salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.5 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

A

azthreonam
78110-38-0

azthreonam

B

3,3-dimethyltetrahydrofuran
15833-75-7

3,3-dimethyltetrahydrofuran

C

Trimethylacetic acid
75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 1.17 h / 37 °C / Enzymatic reaction
View Scheme
4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

4-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate mesylate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.03 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.33 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

5-((((2S,3S)-3-amino-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate mesylate

A

γ,γ-dimethyl-δ-valerolactone
1679-55-6

γ,γ-dimethyl-δ-valerolactone

B

5-hydroxy-4,4-dimethylpentanoic acid
1148130-26-0

5-hydroxy-4,4-dimethylpentanoic acid

C

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 19 h / 37 °C / Enzymatic reaction
View Scheme
(Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid
86299-47-0

(Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C
2.1: dichloromethane / 20 °C
2.2: 0.5 h
3.1: carboxylesterase 1 (CES1) / acetonitrile / 0.5 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
C24H37N5O10S2*C2HF3O2

C24H37N5O10S2*C2HF3O2

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: carboxylesterase 1 (CES1) / acetonitrile / 0.5 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetic acid salt

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((3-ethoxy-2,2-dimethyl-3-oxopropoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetic acid salt

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With carboxylesterase 1 (CES1) In acetonitrile at 37℃; for 0.5h; pH=4.7; Enzymatic reaction;28 %Chromat.
4-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate trifluoroacetate

4-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-3,3-dimethylbutyl pivalate trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: carboxylesterase 1 (CES1) / acetonitrile / 0.03 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 1.17 h / 37 °C / Enzymatic reaction
View Scheme
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

A

azthreonam
78110-38-0

azthreonam

B

3,3-dimethyltetrahydrofuran
15833-75-7

3,3-dimethyltetrahydrofuran

C

Trimethylacetic acid
75-98-9

Trimethylacetic acid

Conditions
ConditionsYield
With sodium dihydrogenphosphate In [D3]acetonitrile; water-d2 at 37℃; for 1.16667h; Mechanism; Enzymatic reaction;
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-((2,2-dimethyl-4-(pivaloyloxy)butoxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With carboxylesterase 1 (CES1) In acetonitrile at 37℃; for 0.0333333h; pH=4.7; Enzymatic reaction;> 95 %Chromat.
ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: carboxylesterase 1 (CES1) / acetonitrile / 0.33 h / 37 °C / pH 4.7 / Enzymatic reaction
View Scheme
ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

ethyl 5-((((2S,3S)-3-((Z)-2-(2-aminothiazol-4-yl)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)acetamido)-2-methyl-4-oxoazetidin-1-yl)sulfonyl)oxy)-4,4-dimethylpentanoate trifluoroacetate

A

γ,γ-dimethyl-δ-valerolactone
1679-55-6

γ,γ-dimethyl-δ-valerolactone

B

5-hydroxy-4,4-dimethylpentanoic acid
1148130-26-0

5-hydroxy-4,4-dimethylpentanoic acid

C

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dichloromethane / 20 °C
1.2: 0.5 h
2.1: sodium dihydrogenphosphate / water-d2; [D3]acetonitrile / 19 h / 37 °C / Enzymatic reaction
View Scheme
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With carboxylesterase 1 (CES1) In acetonitrile at 37℃; for 0.333333h; pH=4.7; Enzymatic reaction;90 %Chromat.
2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

2-(((Z)-(1-(2-aminothiazol-4-yl)-2-(((2S,3S)-1-(((5-ethoxy-2,2-dimethyl-5-oxopentyl)oxy)sulfonyl)-2-methyl-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid trifluoroacetate

A

γ,γ-dimethyl-δ-valerolactone
1679-55-6

γ,γ-dimethyl-δ-valerolactone

B

5-hydroxy-4,4-dimethylpentanoic acid
1148130-26-0

5-hydroxy-4,4-dimethylpentanoic acid

C

azthreonam
78110-38-0

azthreonam

Conditions
ConditionsYield
With sodium dihydrogenphosphate In [D3]acetonitrile; water-d2 at 37℃; for 19h; Mechanism; Enzymatic reaction;
L-lysine
56-87-1

L-lysine

azthreonam
78110-38-0

azthreonam

aztreonam lysinate
827611-49-4

aztreonam lysinate

Conditions
ConditionsYield
In water at 0 - 5℃; Conversion of starting material;77%
In water at 0 - 5℃; Conversion of starting material;62%
In water for 0.1h; pH=4.34; Cooling with ice;56%
In water at 0 - 5℃; Conversion of starting material;
ethanol
64-17-5

ethanol

azthreonam
78110-38-0

azthreonam

aztreonam ethyl ester

aztreonam ethyl ester

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; triethylamine; diisopropyl-carbodiimide at 0 - 32℃; for 48h; Reagent/catalyst;71.6%
azthreonam
78110-38-0

azthreonam

(2S,3S)-2-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-sulfoamino-butyric acid

(2S,3S)-2-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-sulfoamino-butyric acid

Conditions
ConditionsYield
With citrate buffer at 35℃; Rate constant; other aqueous buffer;
With Zn2+-Tris In water at 35℃; Rate constant; other metal ions;
azthreonam
78110-38-0

azthreonam

C12H14N3O5S(1-)*Na(1+)

C12H14N3O5S(1-)*Na(1+)

Conditions
ConditionsYield
With phosphoric acid In water at 35℃; Rate constant; various pH;
azthreonam
78110-38-0

azthreonam

aztreonam

aztreonam

Conditions
ConditionsYield
With water at 59.85℃; Kinetics; Thermodynamic data; Further Variations:; Temperatures;
azthreonam
78110-38-0

azthreonam

[2S-[2α,3β(Z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, 2-[(1,4-dihydro-6,7-dihydroxy-4-oxo-3-quinolinyl)carbonyl]hydrazide, monopotassium salt

[2S-[2α,3β(Z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, 2-[(1,4-dihydro-6,7-dihydroxy-4-oxo-3-quinolinyl)carbonyl]hydrazide, monopotassium salt

Conditions
ConditionsYield
In N-methyl-acetamide

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