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

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

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

1-Azetidinesulfonicacid, 3-amino-2-methyl-4-oxo-, (2S-trans)-;

Article Data 15

(2S-trans)-3-Amino-2-methyl-4-oxoazetidine-1-sulphonic acid 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
ConditionsYield
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
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol50%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
Yield given. Multistep reaction;

C34H69N3O6S

80082-65-1

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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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%

(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 .

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