80082-65-1 (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid AKSci K423
 
 
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  K423    
(2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid
, 98% (HPLC)
 



IDENTITY
CAS Number:80082-65-1
MDL Number:MFCD03425480
MF:C4H8N2O4S
MW:180.18
EINECS:279-393-8
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:98% (HPLC)
Spectra:FT-IR, LCMS, HPLC
Physical Form:White to almost white powder
Melting Point:300°C (dec.)
Long-Term Storage:Store at room temperature
HAZARDOUS MATERIALS INFORMATION
Not hazardous material

REVIEW

 (2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid is a key intermediate in the preparation of aztreonam. Aztreonam is a synthetic monocyclic beta-lactam antibiotic with the nucleus based on a simpler monobactam isolated from Chromobacterium violaceum. It is resistant to some beta-lactamases, but is inactivated by extended-spectrum beta-lactamases.

REFERENCES
[1]Floyd, David M.; Fritz, Alan W.; Cimarusti, Christopher M Monobactams. Stereospecific synthesis of (S)-3-amino-2-oxoazetidine-1-sulfonic acids Journal of Organic Chemistry (1982), 47(1), 176-8.
[2] Floyd, David M.; Fritz, Alan W.; Pluscec, Josip; Weaver, Eugene R.; Cimarusti, Christopher M. Monobactams. Preparation of (S)-3-amino-2-oxoazetidine-1-sulfonic acids from L-alpha-amino-beta-hydroxy acids via their hydroxamic esters Journal of Organic Chemistry (1982), 47(26), 5160-7.
[3] Cimarusti, C. M.; Bonner, D. P.; Breuer, H.; Chang, H. W.; Fritz, A. W.; Floyd, D. M.; Kissick, T. P.; Koster, W. H.; Kronenthal, D.; et al. 4-Alkylated monobactams. Chiral synthesis and antibacterial activity Tetrahedron (1983), 39(15), 2577-89.
[4] Herranz, Rosario; Conde, Santiago; Fernandez-Resa, Piedad; Arribas, Enrique Enantioselective synthesis of (3S)-trans-4-(substituted methyl)monobactams from 2,3-O-isopropylidene-D-glyceraldehyde Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1988), (3), 649-55.

GHS

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501


Current as of April 22, 2021


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CATEGORIES

 APIs and Bioactives > beta-Lactams


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