80082-65-1

Basic information

• Product Name: (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid
• Synonyms: (3S-TRANS)-3-AMINO-4-METHYL-2-OXO-1-AZETINESULFONIC ACID;(2S, 3S)-3-Amino-2-methyl-4-oxoazetidine-1-sulfonic acid;SQ-26771;(2S,3S)-3-azanyl-2-methyl-4-oxo-azetidine-1-sulfonic acid;(3S,4S)-3-amino-2-keto-4-methyl-azetidine-1-sulfonic acid;(2R,3S)-3-Amino-2-me;(2S)-3-aMino-2-Methyl-4-oxoazetidine-1-sulfonic acid;(2R,3S)-3-aMino-2-Methyl-4-oxoazetidine-1-sulfonic acid
• CAS NO: 80082-65-1
• Molecular Formula: C₄H₈N₂O₄S
• Molecular Weight: 180.18
• EINECS: 279-393-8
• Product Categories: AZTREONAM;(intermediate of aztreonam);(intermediate of azetronam);Miscellaneous Reagents;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Amines
• Mol File: 80082-65-1.mol

Chemical Properties

• Melting Point: 206-211°C
• Appearance: /
• Density: 1.75 g/cm³
• Refractive Index: 1.627
• Storage Temp.: -20°C Freezer
• Solubility: Water
• PKA: -0.94±0.40(Predicted)
• CAS DataBase Reference: (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid(80082-65-1)
• EPA Substance Registry System: (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid(80082-65-1)

Safety Data

• Hazardous Substances Data: 80082-65-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid is used as a key intermediate for the synthesis of ?-lactams, a class of antibiotics known for their broad-spectrum antimicrobial activity. Its role in the production of these antibiotics is crucial for developing effective treatments against bacterial infections.
Additionally, (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid is used as an aztreonam intermediate. Aztreonam is a monobactam antibiotic that is effective against a wide range of gram-negative bacteria, including Pseudomonas aeruginosa. The use of this intermediate in the synthesis of aztreonam contributes to the development of potent antibiotics for treating severe bacterial infections.

InChI:InChI=1/C4H8N2O4S/c1-2-3(5)4(7)6(2)11(8,9)10/h2-3H,5H2,1H3,(H,8,9,10)/t2-,3-/m0/s1

Synthetic route

(3S)-trans-3-<(tert-butoxycarbonyl)amino>-4-methyl-2-oxoazetidine-1-sulfonic acid tetra-n-butylammonium salt (80082-60-6) → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
With formic acid for 4.5h; Ambient temperature;	93%
With formic acid for 5h;	70%
With formic acid for 5h; Ambient temperature;	56%

(3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-62-8) → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	50%

tetrabutylammonium (3S,4S)-3-phenylacetamido-4-methyl-2-oxoazetidine-1-sulfonate (80082-64-0) → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
With pyridine; phosgene In dichloromethane at 0℃; for 41h;

(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7) → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; water for 2h; Ambient temperature;
With nitrogen; palladium In methanol; water
With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol; water for 2h; pH=6.8 - 7;
Stage #1: (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt With 5%-palladium/activated carbon; hydrogen In methanol at 15℃; for 4h; Large scale; Stage #2: With hydrogenchloride In methanol; water at 0℃; for 6h; Large scale;

(3S,trans)-4-methyl-3-triphenylmethylamino-2-azetidinone (88144-19-8) → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
Yield given. Multistep reaction;

C34H69N3O6S → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
With formic acid at 35 - 40℃; for 4.5h; Inert atmosphere;	12.7 g

C12H27N*C13H14N2O6S → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
With ammonia; lithium at -40℃; for 0.5h;	56 g

C10H19N2O9S2(1-)*Na(1+) → (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1)

Conditions	Yield
Stage #1: C10H19N2O9S2(1-)*Na(1+) at 45℃; for 1.5h; Stage #2: With sulfuric acid at 30℃; for 6h;	60 g

tetra(n-butyl)ammonium hydroxide (2052-49-5) + N-(benzyloxycarbonyl)succinimide (75315-63-8) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-62-8)

Conditions	Yield
Stage #1: N-(benzyloxycarbonyl)succinimide; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid With triethylamine In ethanol; water at 25℃; for 16h; Stage #2: tetra(n-butyl)ammonium hydroxide In water	94%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + tetra(n-butyl)ammonium hydroxide (2052-49-5) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-62-8)

Conditions	Yield
Stage #1: N-(Benzyloxycarbonyloxy)succinimide; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid With triethylamine In ethanol; water at 20℃; for 16h; Stage #2: tetra(n-butyl)ammonium hydroxide In water	94%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (E)-α-(3-Chloroisoxazol-5-yl)-α-methoxyiminoacetic acid (147742-76-5) → sodium (3S,4S)-3-<(E)-(3-chloroisoxazol-5-yl)(methoxyimino)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 3 d, 2.) H2O, CH3OH;	91%

(isoxazol-3-yl)acetic acid (57612-86-9) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → sodium (3S,4S)-3-<(isoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 3 d, 2.) H2O, CH3OH;	87%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + 3-chloro-5-isoxazolecarboxylic acid chloride (104164-45-6) → sodium (3S,4S)-3-<(3-chloroisoxazol-5-yl)carbonylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 0 to 5 deg C, 1 h, 2.) H2O;	87%

(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) → azthreonam (78110-38-0)

Conditions	Yield
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%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (Z)-2-(((1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydropyridin-2-yl)methoxy)imino)-2-(2-(tritylamino)thiazol-4-yl)acetic acid (114875-61-5) → (3S)-trans-3-[[2-(2-tritylamino)thiazol-4-yl]-(Z)-2-{(1,5-dibenzhydryloxy-4-pyridon-2-ylmethoxy)imino}acetamido]-4-methyl-2-oxoazetidine-1-sulfonic acid (404824-78-8)

Conditions	Yield
Stage #1: (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid; (Z)-2-(((1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydropyridin-2-yl)methoxy)imino)-2-(2-(tritylamino)thiazol-4-yl)acetic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 20℃;	85.9%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + triethylamine (121-44-8) + (S)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester → (2S,3S)-3-{(S)-3-(3,4-Dihydroxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonic acid; compound with triethyl-amine

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 3h; Acylation;	84%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (5-methoxyisoxazol-3-yl)acetic acid → sodium (3S,4S)-3-<(5-methoxyisoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 3 d, 2.) H2O, CH3OH;	82%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (5-chloroisoxazol-3-yl)acetic acid → sodium (3S,4S)-3-<(5-chloroisoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 3 d, 2.) H2O, CH3OH;	81%

(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)

Conditions	Yield
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%

C35H38N4O6S2 + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → (2S,3S)-3-{(S,Z)-5-(tert-butoxycarbonyl)-7-oxo-11-[2-(tritylamino)thiazol-4-yl]- 9-oxa-2-thia-6,10-diazadodec-10-enamido}-2-methyl-4-oxoazetidine-1-sulfonic acid

Conditions	Yield
Stage #1: C35H38N4O6S2 With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid With triethylamine In N,N-dimethyl-formamide at 20℃;	78%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (3-Chloroisoxazol-5-yl)acetic acid (54489-25-7) → sodium (3S,4S)-<(3-chloroisoxazol-5-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 24 h, 2.) H2O, CH3OH;	75%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (4-Cyano-5-methylisoxazol-3-yl)acetic acid (93276-75-6) → sodium (3S,4S)-3-<(4-cyano-5-methylisoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 24 h, 2.) H2O, CH3OH;	73%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + (Z)-α-(3-Chloroisoxazol-5-yl)-α-methoxyiminoacetic acid (147742-85-6) → sodium (3S,4S)-3-<(Z)-(3-chloroisoxazol-5-yl)(methoxyimino)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 3 d, 2.) H2O, CH3OH;	62%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + triethylamine (121-44-8) + (3,4-dihydroxy-phenylsulfanyl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester → (2S,3S)-3-[2-(3,4-Dihydroxy-phenylsulfanyl)-acetylamino]-2-methyl-4-oxo-azetidine-1-sulfonic acid; compound with triethyl-amine

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 3h; Acylation;	59%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + α-tert-Butyloxycarbonylamino-α-(3-chloroisoxazol-5-yl)acetic Acid (147742-81-2) → sodium (3S,4S)-3-<(tert-butoxycarbonylamino)(3-chloroisoxazol-5-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions	Yield
With ion exchange column (Na form); benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 3 d, 2.) H2O, CH3OH;	57%

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) + triethylamine (121-44-8) + (2-tert-butoxycarbonylamino-thiazol-4-yl)-[4-(N'-tert-butoxycarbonyl-hydrazinocarbonyl)-benzyloxyimino]-acetic acid [1,2,3]triazolo[4,5-b]pyridin-3-yl ester → trans-3-[(Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]-2-[[4-[[2-(tert-butoxycarbonyl)hydrazino]carbonyl]benzyloxy]imino]acetamido]-4-methyl-2-oxoazetidine-1-sulfonic acid triethylammonium salt

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Acylation;	53%

α-methyl-4-chlorobenzylideneaminoxy propionic acid (63564-50-1) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → Sodium; (2S,3S)-3-{3-[1-(4-chloro-phenyl)-eth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate (134468-86-3)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1) DMF, 30 min, r.t 2) DMF, 18h, r.t.; Yield given. Multistep reaction;

3-(isopropylidenamino)oxy-propanoic acid (103586-55-6) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → Sodium; (2S,3S)-3-(3-isopropylideneaminooxy-propionylamino)-2-methyl-4-oxo-azetidine-1-sulfonate (134468-81-8)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1) DMF, 30 min, r.t 2) DMF, 18h, r.t.; Yield given. Multistep reaction;

3-(1-Propyl-butylideneaminooxy)-propionic acid (103586-56-7) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → Sodium; (2S,3S)-2-methyl-4-oxo-3-[3-(1-propyl-butylideneaminooxy)-propionylamino]-azetidine-1-sulfonate (134468-83-0)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1) DMF, 30 min, r.t 2) DMF, 18h, r.t.; Yield given. Multistep reaction;

3-Cyclopentylideneaminooxy-propionic acid (103586-53-4) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → Sodium; (2S,3S)-3-(3-cyclopentylideneaminooxy-propionylamino)-2-methyl-4-oxo-azetidine-1-sulfonate (134468-82-9)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1) DMF, 30 min, r.t 2) DMF, 18h, r.t.; Yield given. Multistep reaction;

3-[1-Phenyl-eth-(E)-ylideneaminooxy]-propionic acid (103586-52-3) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → Sodium; (2S,3S)-2-methyl-4-oxo-3-{3-[1-phenyl-eth-(E)-ylideneaminooxy]-propionylamino}-azetidine-1-sulfonate (134468-85-2)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1) DMF, 30 min, r.t 2) DMF, 18h, r.t.; Yield given. Multistep reaction;

(E)-3-<(benzylidene)iminoxy>-(E)-2-(methoxyimino)propionic acid (110596-23-1) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-phenyl-meth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate (134468-87-4)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1) DMF, 30 min, r.t 2) DMF, 18h, r.t.; Yield given. Multistep reaction;

(E)-3-<<(benzylidene)methyl>iminoxy>-(E)-2-(methoxyimino)propionic acid (110596-24-2) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-phenyl-eth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate (134468-91-0)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide 1) DMF, 30 min, r.t 2) DMF, 18h, r.t.; Yield given. Multistep reaction;

Upstream product

• 80082-64-0 tetrabutylammonium (3S,4S)-3-phenylacetamido-4-methyl-2-oxoazetidine-1-sulfonate 
• 80082-60-6 (3S)-trans-3-<(tert-butoxycarbonyl)amino>-4-methyl-2-oxoazetidine-1-sulfonic acid tetra-n-butylammonium salt 
• 80082-62-8 (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt 
• 115887-91-7 (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt 
• 88144-19-8 (3S,trans)-4-methyl-3-triphenylmethylamino-2-azetidinone 
• 122553-92-8 cis-4-methyl-3-phenylacetylamino-2-oxoazetidine-1-sulphonic acid sodium salt 
• 115887-91-7 cis-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt 

Downstream Products

• 134468-86-3 Sodium; (2S,3S)-3-{3-[1-(4-chloro-phenyl)-eth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate 
• 134468-85-2 Sodium; (2S,3S)-2-methyl-4-oxo-3-{3-[1-phenyl-eth-(E)-ylideneaminooxy]-propionylamino}-azetidine-1-sulfonate 
• 134468-87-4 Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-phenyl-meth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate 
• 134468-91-0 Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-phenyl-eth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate 
• 134468-88-5 Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-(4-methoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate 
• 134468-89-6 Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-(2-methoxy-phenyl)-meth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate 
• 134468-92-1 Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-(4-methoxy-phenyl)-eth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate 
• 123539-91-3 3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid 
• 404824-78-8 (3S)-trans-3-[[2-(2-tritylamino)thiazol-4-yl]-(Z)-2-{(1,5-dibenzhydryloxy-4-pyridon-2-ylmethoxy)imino}acetamido]-4-methyl-2-oxoazetidine-1-sulfonic 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 
• 149-30-4 2-Mercaptobenzothiazole 
• 941286-30-2 (3S,4S)-3-((2Z)-3-{[5-(diphenylmethoxy)-1-methyl-4-oxo-(2-hydropyridyl)]methoxy}-2-{2-[(triphenylmethyl)amino](1,3-thiazol-4-yl)}-3-azaprop-2-enoylamino)-4-methyl-2-oxoazetidinesulfonic acid 
• 78110-38-0 azthreonam 
• 80082-62-8 (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt 

Relevant articles and documents

Synthesis method of aztreonam monocyclic mother nucleus

The invention discloses a synthesis method of an aztreonam monocyclic mother nucleus, and mainly relates to the technical field of pharmaceutical and chemical industry. The method comprises the stepsthat L-threonine is subjected to methyl esterification; terbutyloxycarbonyl anhydride is used for performing amino BOC protection; ammonia water is subjected to ammonolysis; under the catalysis of a solid basic catalyst, methyl-sulfuric-acyl reaction and sulfonation are performed; cyclization, deprotection and acidification are performed to obtain the aztreonam monocyclic mother nucleus. The raw materials are cheap and can be easily obtained; the yield is high; the cost is low; the synthesis method belongs to a green, energy-saving and environment-friendly practical technology.

Synthetic method for aztreonam mother nucleus

The invention provides a synthetic method for an aztreonam mother nucleus. The method uses sulfamic acid and ethyl bromoacetate as starting raw materials and produces the aztreonam mother nucleus through a chiral prosthetic group-induced 2+2 addition reaction. The method has the advantages of low price of raw materials and high yield, and does not use the high-risk chemical chlorosulfonic acid.

Aztreonam primary ring synthesis method

The invention discloses a synthesis method of an aztreonam main ring, which comprises the following steps: by using L-threonine as a raw material, carrying out amino protection, converting carboxyl group into amido sulfonic acid, carrying out cyclization reaction, and finally deprotecting to obtain the aztreonam main ring. The method is simple to operate and lower in cost, and the total yield is 48.7%. The produced aztreonam main ring is white solid powder, the specific rotatory power is -45 degrees, and the HPLC (high performance liquid chromatography) purity is 98.5% above. The quality of the product is high, and thus, the method is suitable for industrial production.

Ammonia curved the monocyclic parent nucleus method for the preparation of

The invention relates to a preparation of Aztreonam monocyclic parent nucleus method, in the method using benzyl chloroformate under strongly acidic conditions the protection, the sodium carbonate is used to carry out closed-loop reaction, the reaction is stable, is greatly improved yield, total yield of 48% the advantages.

USEFUL COMBINATIONS OF MONOBACTAM ANTIBIOTICS WITH BETA-LACTAMASE INHIBITORS

A pharmaceutical composition, comprising a combination of an antibiotically active compound of the formula (I): with a ?-lactamase inhibitor of one of the formulae (II) to (XIII) are active against Gram-negative bacteria, in particular such bacteria which have become resistant against antibiotics such as aztreonam, carumonam and tigemonam. Optionally the compositions may comprise another ?-lactamase inhibitor of one of the formulae (II) to (XIII), particularly of formula (V) or formula (VI).

Regioselective activation of aminothiazole(iminoxyacetic acid)acetic acid: An efficient synthesis of the monobactam aztreonam

An efficient synthesis of the monobactam aztreonam [[2S-[2α,3β(Z)]]-3[[(2-amino-4-thiazolyl)[(1-carboxy-1- methylethoxy)imino]acetyl]amino]-2-methyl-4-oxo-1-azetidinesulfonic acid] (1) by acylation of α-aminoazetidinone 22 with the regioselectively activated aminothiazoleiminoxyacetic diacid 15 or 18 is described. Reaction of benzhydryl ester 10 with N-hydroxy-benzotriazole and dicyclohexylcarbodiimide followed by ester deprotection formed the monoacid amide 15. Alternatively, chemoselective transient silylation of the diacid 9 followed by activation with N-hydroxysuccinimide formed active ester 18. Acylation of α-aminoazetidinone 22 with amide 15 or ester 18 produced aztreonam (1) in 75-85% yield.

Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains

Disclosed herein are processes for preparing a compound of the formula STR1 in which a novel compound of the formula STR2 is reacted with a beta lactam of the formula STR3 by treatment with a base, wherein the symbols are as defined in the specification.

Stereoselective synthesis of cis-4-(substituted) monobactams from ethyl acetoacetate

The stereoselective synthesis of cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid (25) from ethyl acetoacetate is described. Nitrosation of this compound and reduction of the resulting oxime gave the corresponding amine, which after treatment with different acyl halides, yielded the acylamino derivatives (6)-(8). Condensation with p-anisidine gave the enamines (12)-(14), which were then reduced to the β-amino acid esters (15)-(17). Stereoselective cyclization with Grignard reagents as base, and appropriate deprotection and sulphonation of the resulting β-lactams (18)-(20), led to the title compounds.

2-OXO-1-AZETIDINESULFONIC ACID SALTS

Antibacterial activity is exhibited by beta-lactams having a sulfonic acid salt substituent in the 1-position and an amino or acylamino substituent in the 3-position.

Enantioselective Synthesis of (3S)-trans-4-(Substituted Methyl)monobactams from 2,3-O-Isopropylidene-D-glyceraldehyde

The enantioselective synthesis of various (3S)-trans-4-(substituted methyl)-2-oxoazetidine-1-sulphonic acid derivatives from 2,3-O-isopropylidene-D-glyceraldehyde is described.Reaction of this aldehyde with trimethylsilyl cyanide gave a 80:20 ratio of the corresponding threo and erythro α-amino-nitriles, which by amino protection and subsequent treatment with basic hydrogen peroxide provided the corresponding α-amino carboxamides.Successive selective protection, activation, sulphonation and, finally, stereospecific cyclization of the threo α-carboxamide yielded (2S,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid, an intermediate for the synthesis of the corresponding 4-acyloxymethyl-, 4-carbamoyloxymethyl-, 4-methylsulphonyloxy-methyl-, 4-iodomethyl-, and 4-methyl-2-oxozetidines.