Amoxicillin and clavulanic acid

Base Information

• Chemical Name: Amoxicillin and clavulanic acid
• CAS No.: 79198-29-1
• Deprecated CAS: 142901-08-4
• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.295
• DSSTox Substance ID: DTXSID80872429
• ChEMBL ID: CHEMBL2097107
• Mol file: 79198-29-1.mol

Synonyms:amoxicillin + clavulanic acid;79198-29-1;Amoxicillin and clavulanic acid;Amoxicillin + clavulinic acid;Amoxicillin clavulanate;Amoxyclav;Augmentin (free acid);Amoxicillin clavulanate acid;(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Amoxicillin-clavulanic acid mixt.;Clavulanic acid - amoxicillin mixt.;Amoksiclav;Amoxicillin & Clavulanate;Amoxicillin & Clavulanic acid;SCHEMBL591660;CHEMBL2097107;DTXSID80872429;NCGC00188989-01;4-Oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2R,3Z,5R)-, mixt. with (2S,5R,6R)-6-(((2R)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid;4-Oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2R-(2alpha,3Z,5alpha))-, mixt. with (2S-(2alpha,5alpha,6beta(S*))-6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid

Chemical Property of Amoxicillin and clavulanic acid

Chemical Property:

• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 564.15261428
• Heavy Atom Count: 39
• Complexity: 914

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C.C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C.C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
• Recent ClinicalTrials: Pharmacokinetics and Pleural Fluid Penetration of Amoxicillin and Clavulanic Acid in Patients With Pleural Infections
• Recent EU Clinical Trials: Evaluation of Amoxicillin diffusion in breast milk according to a population pharmacokinetic approach.

Technology Process of Amoxicillin and clavulanic acid

There total 9 articles about Amoxicillin and clavulanic 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: 36.0%

(-)-2,3,3aS,8aR-tetrahydro-4-hydroxy-6-methoxy[2,3-d]-benzo[b]furan (6795-22-8) + ethyl 2-bromo-5-oxocyclopent-1-enecarboxylate (30694-05-4) → aflatoxin B2 (7220-81-7)

Guidance literature:

With sodium hydrogencarbonate; zinc(II) carbonate; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1021/ja054503m

Reference yield:

2-methoxy-1,4-benzoquinone (2880-58-2) → aflatoxin B2 (7220-81-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (R)-α,α-diphenyl-2-pyrrolidinemethanol derived catalyst / acetonitrile / 5 h / 20 °C

2.1: AcOH / 48 h / 110 °C

2.2: 40 percent / aq. H₂SO₄ / 1 h / 75 °C

3.1: 80 percent / DMAP; pyridine / CH₂Cl₂ / 2 h / 0 °C

4.1: tetrahydrofuran; diethyl ether / 2 h / -20 °C

5.1: 162 mg / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

6.1: 62.5 percent / urea-H₂O₂ complex; trifluoroacetic anhydride / CH₂Cl₂ / 48 h / 20 °C

7.1: 60 percent / H₂; Raney nickel / methanol / 3 h / 20 °C

8.1: 36 percent / NaHCO₃; ZnCO₃ / CH₂Cl₂ / 20 h / 20 °C

With pyridine; dmap; (R)-α,α-diphenyl-2-pyrrolidinemethanol derived catalyst; hydrogen; urea hydrogen peroxide adduct; nickel; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; zinc(II) carbonate; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 5.1: Dess-Martin oxidation / 6.1: Baeyer-Villiger oxidation;

DOI:10.1021/ja054503m

Reference yield:

(-)-cis-5-trifluoromethanesulfonyloxy-2,3,3aS,8aR-tetrahydro-6-methoxy[2,3-d]-benzo[b]furan-4-carboxaldehyde (865811-99-0) → aflatoxin B2 (7220-81-7)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran; diethyl ether / 2 h / -20 °C

2: 162 mg / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

3: 62.5 percent / urea-H₂O₂ complex; trifluoroacetic anhydride / CH₂Cl₂ / 48 h / 20 °C

4: 60 percent / H₂; Raney nickel / methanol / 3 h / 20 °C

5: 36 percent / NaHCO₃; ZnCO₃ / CH₂Cl₂ / 20 h / 20 °C

With hydrogen; urea hydrogen peroxide adduct; nickel; sodium hydrogencarbonate; Dess-Martin periodane; zinc(II) carbonate; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2: Dess-Martin oxidation / 3: Baeyer-Villiger oxidation;

DOI:10.1021/ja054503m

upstream raw materials:

aflatoxin B₁

(-)-2,3,3aS,8aR-tetrahydro-4-hydroxy-6-methoxy[2,3-d]-benzo[b]furan

ethyl 2-bromo-5-oxocyclopent-1-enecarboxylate

(-)-cis-5-trifluoromethanesulfonyloxy-2,3,3aS,8aR-tetrahydro-6-methoxy[2,3-d]-benzo[b]furan-4-carboxaldehyde

Refernces

• 1、 Shukla, Ram S.,Verma, Ramtej J.,Mehta, Daxa N.. "Kinetic and mechanistic investigations on reductions of aflatoxins by lactic acid". . p. 2737 - 2741. Retrieved 2007/10/03.