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

Base Information

• Chemical Name: (2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid
• CAS No.: 80582-09-8
• Molecular Formula: C4H8N2O4S
• Molecular Weight: 180.185
• DSSTox Substance ID: DTXSID10454611
• Mol file: 80582-09-8.mol

Synonyms:80582-09-8;(2R,3S)-3-AMINO-2-METHYL-4-OXO-1-AZETIDINESULFONIC ACID;(2R,3S)-3-Amino-2-methyl-4-oxoazetidine-1-sulfonic acid;(2S,3S)-3-AMINO-2-METHYL-4-OXO-1-AZETIDINESULFONIC ACID;SCHEMBL8311599;DTXSID10454611;AKOS006277543;W-104251;(3S-cis)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid

Chemical Property of (2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

Chemical Property:

• PSA: 109.08000
• LogP: 0.06620
• XLogP3: -3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 180.02047791
• Heavy Atom Count: 11
• Complexity: 279

Purity/Quality:

98.5% ^*data from raw suppliers

(2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

There total 2 articles about (2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

cis-4-methyl-3-phenylacetylamino-2-oxoazetidine-1-sulphonic acid sodium salt (122553-92-8) → cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid (80082-65-1,80582-09-8,92007-69-7,95586-88-2,112026-42-3,122553-93-9)

Guidance literature:

With immobilized Penicillin G acylase; at 37 ℃; for 0.5h; pH 8 buffer phosphate;

Reference yield: 78.0%

cis-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt (115887-91-7,122553-91-7) → cis-3-amino-4-methyl-2-oxoazetidine-1-sulphonic acid (80082-65-1,80582-09-8,92007-69-7,95586-88-2,112026-42-3,122553-93-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; for 2h; Ambient temperature; atmospheric pressure;

Reference yield: 94.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + tetra(n-butyl)ammonium hydroxide (2052-49-5) + (2R-cis)-3-amino-2-methyl-4-oxo-1-azetidine-sulfonic acid (80582-09-8) → (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-62-8)

Guidance literature:

N-(Benzyloxycarbonyloxy)succinimide; (2R-cis)-3-amino-2-methyl-4-oxo-1-azetidine-sulfonic acid; With triethylamine; In ethanol; water; at 25 ℃; for 16h;

tetra(n-butyl)ammonium hydroxide; In water;

upstream raw materials:

cis-4-methyl-3-phenylacetylamino-2-oxoazetidine-1-sulphonic acid sodium salt

cis-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt

Downstream raw materials:

(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

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

Refernces