80582-09-8

Basic information

• Product Name: (2R,3S)-3-AMino-2-Methyl-4-oxo-1-azetidinesulfonic Acid
• Synonyms: AztreomImpurity21;Aztreonam Impurity 36;1-Azetidinesulfonic acid, 3-amino-2-methyl-4-oxo-, (2R,3S)-
• CAS NO: 80582-09-8
• Molecular Formula: C₄H₈N₂O₄S
• Molecular Weight: 180.18232
• Product Categories: Amines;Chiral Reagents;Miscellaneous Reagents
• Mol File: 80582-09-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R,3S)-3-AMino-2-Methyl-4-oxo-1-azetidinesulfonic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-AMino-2-Methyl-4-oxo-1-azetidinesulfonic Acid(80582-09-8)
• EPA Substance Registry System: (2R,3S)-3-AMino-2-Methyl-4-oxo-1-azetidinesulfonic Acid(80582-09-8)

Safety Data

• Hazardous Substances Data: 80582-09-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(2R,3S)-3-AMino-2-Methyl-4-oxo-1-azetidinesulfonic Acid is a useful intermediate in the preparation of Lactams.

Upstream product

• 115887-91-7 cis-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt 
• 122553-92-8 cis-4-methyl-3-phenylacetylamino-2-oxoazetidine-1-sulphonic acid sodium salt 

Downstream Products

• 80082-62-8 (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt 
• 263154-24-1 (2R,3S)-3-{2-[(Z)-4-Benzothiazol-2-yl-3-methoxymethoxy-benzyloxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-2-methyl-4-oxo-azetidine-1-sulfonic acid 

Relevant articles and documents

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.