Nocardicin A

Base Information

• Chemical Name: Nocardicin A
• CAS No.: 39391-39-4
• Molecular Formula: C23H24N4O9
• Molecular Weight: 500.465
• UNII: R76HLW7Z19
• DSSTox Substance ID: DTXSID201028178
• Nikkaji Number: J18.342C
• Wikipedia: Nocardicin_A
• Wikidata: Q4981302
• Metabolomics Workbench ID: 51012
• Mol file: 39391-39-4.mol

Synonyms:nocarcidins;nocardicin;nocardicin A;nocardicin A, sodium salt;nocardicin B

Chemical Property of Nocardicin A

Chemical Property:

• Melting Point: 214-216° (dec)
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 591.34°C (rough estimate)
• PSA: 212.08000
• Density: 1.57g/cm³
• LogP: 0.93330
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 500.15432836
• Heavy Atom Count: 36
• Complexity: 851

Purity/Quality:

99% ,98%,Electron Grade , ^*data from raw suppliers

Nocardicin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)N1C(C2=CC=C(C=C2)O)C(=O)O)NC(=O)C(=NO)C3=CC=C(C=C3)OCCC(C(=O)O)N
• Isomeric SMILES: C1[C@@H](C(=O)N1[C@H](C2=CC=C(C=C2)O)C(=O)O)NC(=O)/C(=N\O)/C3=CC=C(C=C3)OCC[C@H](C(=O)O)N
• Uses: Nocardicin A is a β-lactam antibiotic.

Technology Process of Nocardicin A

There total 28 articles about Nocardicin A 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: 67.0%

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin A (110269-45-9,110207-52-8) → (-)-nocardicin B (60134-71-6,39391-39-4)

Guidance literature:

With trifluoroacetic acid; 2-hydroxyethanethiol; for 0.116667h; Ambient temperature;

DOI:10.1021/ja00158a040

Reference yield: 67.0%

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin A (110269-45-9,110207-52-8) → (-)-nocardicin A (39391-39-4)

Guidance literature:

With trifluoroacetic acid; 2-hydroxyethanethiol; for 0.116667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)83888-5

Reference yield:

(R)-2-(((benzyloxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid (26787-75-7) → (-)-nocardicin B (60134-71-6,39391-39-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) potassium hydride / 1.) DMF, RT, 10 min, 2.) RT, 3 h

2: 88 percent / 2,6-lutidine, 1-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) RT, 1.5 h

3: 98 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 2068.6 Torr

4: 58 percent / sodium bicarbonate, sodium tungstate, hydrogen peroxide / H₂O; methanol / 6 h

5: 67 percent / 2-mercaptoethanol, trifluoroacetic acid / 0.12 h / Ambient temperature

With 2,6-dimethylpyridine; sodium tungstate; hydrogen; dihydrogen peroxide; potassium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2-hydroxyethanethiol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1021/ja00158a040

upstream raw materials:

di-tert-butyl N-(tert-butoxycarbonyl)nocardicin A

p-benzyloxybenzaldehyde

-propoxy>phenyl>glyoxylic acid

(3R)-α--3-bromo-N-(diphenylmethyl)-2-oxo-1-azetidineacetamide

Downstream raw materials:

D-4-hydroxyphenylglycine

cyclohexanecarboxylic acid-(4-bromo-phenacyl ester)

(R)-2-Amino-4-(4-{((S)-1-carboxy-2-{[(R)-carboxy-(4-hydroxy-phenyl)-methyl]-amino}-ethylcarbamoyl)-[(Z)-hydroxyimino]-methyl}-phenoxy)-butyric acid

p-hydroxyphenylglycine

Refernces

Practical synthetic approaches to intermediates for the preparations of the novel O-sulfonated-N-hydroxy-2-azetidinone antibiotics

10.1016/S0040-4020(01)92150-7

The research focuses on the practical synthesis of intermediates for the preparation of novel 0-sulfonated-N-hydroxy-2-azetidinone antibiotics, which are a class of monocyclic β-lactam antibiotics. The purpose of the study was to develop a simplified and commercially viable synthetic approach to key intermediates for the preparation of these antibiotics, including nocardicins, monobactams, and the new 0-sulfonated N-hydroxy-2-azetidinone antibiotics. The researchers achieved this by hydroxaminolysis of N-protected serine esters to produce hydroxamic acids, followed by acylation and cyclization to yield β-lactams. The process also involved solvolytic deacylation to obtain the parent N-hydroxy-2-azetidinones, which could be further converted to N-unsubstituted 2-azetidinones or the novel 0-sulfonated antibiotics. The chemicals used in the process included N-protected serine esters, hydroxylamine, acyl groups, and various reagents for cyclization and purification steps, such as pyridine-SO3 for the final step to produce the 0-sulfonated N-hydroxy-2-azetidinones. The conclusions of the research indicated that the developed synthetic approach was practical, did not require expensive reagents, and minimized the use of chromatography, making it a potentially commercially viable method for producing these antibiotics.