(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid supplier

Name
(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid
EINECS 279-393-8
CAS No. 80082-65-1
Article Data15
CAS DataBase
Density 1.75 g/cm³
Solubility
Melting Point 206-211oC
Formula C₄H₈N₂O₄S
Boiling Point
Molecular Weight 180.185
Flash Point
Transport Information
Appearance White to white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-Azetidinesulfonicacid, 3-amino-2-methyl-4-oxo-, (2S-trans)-;
PSA 109.08000
LogP 0.06620

Synthetic route

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

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

Conditions

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%

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

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

Conditions

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

: 80082-64-0
tetrabutylammonium (3S,4S)-3-phenylacetamido-4-methyl-2-oxoazetidine-1-sulfonate

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

Conditions

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

: 115887-91-7
(3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt

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

Conditions

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;

: 88144-19-8
(3S,trans)-4-methyl-3-triphenylmethylamino-2-azetidinone

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

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: C34H69N3O6S

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

Conditions

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

: C12H27N*C13H14N2O6S

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

Conditions

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

: C10H19N2O9S2(1-)*Na(1+)

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

Conditions

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

: 2052-49-5
tetra(n-butyl)ammonium hydroxide

: 75315-63-8
N-(benzyloxycarbonyl)succinimide

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

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

Conditions

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%

...Expand

: 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide

: 2052-49-5
tetra(n-butyl)ammonium hydroxide

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

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

Conditions

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%

...Expand

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

: 147742-76-5
(E)-α-(3-Chloroisoxazol-5-yl)-α-methoxyiminoacetic acid

: sodium (3S,4S)-3-<(E)-(3-chloroisoxazol-5-yl)(methoxyimino)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

: 57612-86-9
(isoxazol-3-yl)acetic acid

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

: sodium (3S,4S)-3-<(isoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

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

: 104164-45-6
3-chloro-5-isoxazolecarboxylic acid chloride

: sodium (3S,4S)-3-<(3-chloroisoxazol-5-yl)carbonylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

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

: 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

: 78110-38-0
azthreonam

Conditions

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%

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

: 114875-61-5
(Z)-2-(((1,5-bis(benzhydryloxy)-4-oxo-1,4-dihydropyridin-2-yl)methoxy)imino)-2-(2-(tritylamino)thiazol-4-yl)acetic 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

Conditions

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%

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

: 121-44-8
triethylamine

: (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

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

...Expand

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

: (5-methoxyisoxazol-3-yl)acetic acid

: sodium (3S,4S)-3-<(5-methoxyisoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

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

: (5-chloroisoxazol-3-yl)acetic acid

: sodium (3S,4S)-3-<(5-chloroisoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

: 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

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

: 78110-38-0
azthreonam

Conditions

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

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

: (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

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%

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

: 54489-25-7
(3-Chloroisoxazol-5-yl)acetic acid

: sodium (3S,4S)-<(3-chloroisoxazol-5-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

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

: 93276-75-6
(4-Cyano-5-methylisoxazol-3-yl)acetic acid

: sodium (3S,4S)-3-<(4-cyano-5-methylisoxazol-3-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

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

: 147742-85-6
(Z)-α-(3-Chloroisoxazol-5-yl)-α-methoxyiminoacetic acid

: sodium (3S,4S)-3-<(Z)-(3-chloroisoxazol-5-yl)(methoxyimino)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

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

: 121-44-8
triethylamine

: (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

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

...Expand

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

: 147742-81-2
α-tert-Butyloxycarbonylamino-α-(3-chloroisoxazol-5-yl)acetic Acid

: sodium (3S,4S)-3-<(tert-butoxycarbonylamino)(3-chloroisoxazol-5-yl)acetylamino>-4-methyl-2-oxoazetidine-1-sulfonate

Conditions

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

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

: 121-44-8
triethylamine

: (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

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

...Expand

: 63564-50-1
α-methyl-4-chlorobenzylideneaminoxy propionic acid

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

: 134468-86-3
Sodium; (2S,3S)-3-{3-[1-(4-chloro-phenyl)-eth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate

Conditions

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

: 103586-55-6
3-(isopropylidenamino)oxy-propanoic acid

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

: 134468-81-8
Sodium; (2S,3S)-3-(3-isopropylideneaminooxy-propionylamino)-2-methyl-4-oxo-azetidine-1-sulfonate

Conditions

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

: 103586-56-7
3-(1-Propyl-butylideneaminooxy)-propionic acid

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

: 134468-83-0
Sodium; (2S,3S)-2-methyl-4-oxo-3-[3-(1-propyl-butylideneaminooxy)-propionylamino]-azetidine-1-sulfonate

Conditions

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

: 103586-53-4
3-Cyclopentylideneaminooxy-propionic acid

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

: 134468-82-9
Sodium; (2S,3S)-3-(3-cyclopentylideneaminooxy-propionylamino)-2-methyl-4-oxo-azetidine-1-sulfonate

Conditions

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

: 103586-52-3
3-[1-Phenyl-eth-(E)-ylideneaminooxy]-propionic acid

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

: 134468-85-2
Sodium; (2S,3S)-2-methyl-4-oxo-3-{3-[1-phenyl-eth-(E)-ylideneaminooxy]-propionylamino}-azetidine-1-sulfonate

Conditions

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

: 110596-23-1
(E)-3-<(benzylidene)iminoxy>-(E)-2-(methoxyimino)propionic acid

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

: 134468-87-4
Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-phenyl-meth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate

Conditions

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

: 110596-24-2
(E)-3-<<(benzylidene)methyl>iminoxy>-(E)-2-(methoxyimino)propionic acid

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

: 134468-91-0
Sodium; (2S,3S)-3-{2-[(E)-methoxyimino]-3-[1-phenyl-eth-(E)-ylideneaminooxy]-propionylamino}-2-methyl-4-oxo-azetidine-1-sulfonate

Conditions

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

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid Chemical Properties

IUPAC name: (2S,3S)-3-Amino-2-methyl-4-oxoazetidine-1-sulfonic acid
Molecular Formula: C₄H₈N₂O₄S
Molecular Weight: 180.18 g/mol
The molecular structure of (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid (CAS NO.80082-65-1):

Density: 1.75 g/cm³
EINECS: 279-393-8
Index of Refraction: 1.627
Surface Tension of (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid (CAS NO.80082-65-1): 87.4 dyne/cm
Appearance of (2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid (CAS NO.80082-65-1): White to white powder
Canonical SMILES: CC1C(C(=O)N1S(=O)(=O)O)N
Isomeric SMILES: C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)N
InChI: InChI=1S/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
InChIKey: ISUIVWNWEDIHJD-HRFVKAFMSA-N

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid Uses

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid (CAS NO.80082-65-1) is a useful intermediate in the preparation of Lactams.

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid Specification

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid , its cas register number is 80082-65-1. The chemical synonyms of (2S-Trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid (CAS NO.80082-65-1) are (2s,3s)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid ; (2s-trans)-3-Methyl-4-oxo-1-azetidinesulfonic acid(foraztreonam) ; 3s-trans-3-amino-4-methyl-2-oxo-1-azetidine sulfonic acid ; and 3-Amino-4-methylmonobactamic acid .

Product Name

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid

Synthetic route

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid Chemical Properties

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid Uses

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid Specification

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