L-Amoxicillin

Base Information

• Chemical Name: L-Amoxicillin
• CAS No.: 26889-93-0
• Molecular Formula: C16H19 N3 O5 S
• Molecular Weight: 365.41
• Hs Code.: 2934990002
• NSC Number: 755870
• UNII: 623M8I9SZN
• DSSTox Substance ID: DTXSID30181396
• Nikkaji Number: J661.895B
• Wikidata: Q27167062
• ChEMBL ID: CHEMBL1367635
• Mol file: 26889-93-0.mol

Synonyms:L-Amoxicillin;Amoxicillin, L-;26889-93-0;(2S,5R,6R)-6-((S)-2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;UNII-623M8I9SZN;623M8I9SZN;Amoxicillin trihydrate impurity B [EP];(2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2S)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-, stereoisomer;(2S,5R,6R)-6-[[(2S)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (L-Amoxicillin);4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(R*)))-;CAS-26787-78-0;Spectrum_000048;Spectrum2_000145;Spectrum3_000300;Spectrum4_000148;Spectrum5_000810;BSPBio_001840;KBioGR_000596;KBioSS_000428;DivK1c_000231;SPECTRUM1500120;SPBio_000250;CHEMBL1367635;Amoxicillin trihydrate impurity B;CHEBI:95232;HMS500L13;KBio1_000231;KBio2_000428;KBio2_002996;KBio2_005564;KBio3_001340;DTXSID30181396;NINDS_000231;HMS1920C17;HMS2091I17;Pharmakon1600-01500120;CCG-38922;NSC755870;NSC-755870;IDI1_000231;NCGC00016797-01;NCGC00178966-01;F83935;AB00051914_02;SR-05000001561;AMOXICILLIN SODIUM IMPURITY B [EP IMPURITY];SR-05000001561-1;AMOXICILLIN TRIHYDRATE IMPURITY B [EP IMPURITY];Q27167062;BENZYLPENICILLIN SODIUM IMPURITY C [EP IMPURITY];BENZYLPENICILLIN POTASSIUM IMPURITY C [EP IMPURITY];4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINO(4-HYDROXYPHENYL)ACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(R*)))-

Chemical Property of L-Amoxicillin

Chemical Property:

• Boiling Point: 743.2±60.0 °C(Predicted)
• PKA: 2.44±0.50(Predicted)
• PSA: 161.75000
• Density: 1.54±0.1 g/cm3(Predicted)
• LogP: 1.50220
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Water (Slightly, Heated, Sonicated)
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 365.10454189
• Heavy Atom Count: 25
• Complexity: 590

Purity/Quality:

≧95%, ^*data from raw suppliers

L-Amoxicillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
• 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
• Uses: Isomer of Amoxicillin (A634235), a semi-synthetic antibiotic related to penicillin. Antibacterial. L-Amoxicillin (Amoxicillin EP Impurity B) is an isomer of Amoxicillin (A634235), a semi-synthetic antibiotic related to penicillin.

Technology Process of L-Amoxicillin

There total 2 articles about L-Amoxicillin 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:

→ amoxicillin (26787-78-0,26889-93-0,38083-36-2,98464-36-9,81030-75-3)

Guidance literature:

entspr. Amin, α-Amino-4-hydroxyphenacetylchlorid;

Reference yield:

→ p-Hydroxyampicillin (26787-78-0,26889-93-0,38083-36-2,98464-36-9,81030-75-3)

Guidance literature:

aus 6-Aminopenicillinsaeure, Triethylamin, Trimethylchlorsilan, Ethylenchlorphosphit, D-(-)-p-Hydroxyphenylglycylchlorid*HCl;

Reference yield: 5.0%

amoxycillin trihydrate (26889-93-0,81030-75-3) → amoxicillin (2R)-piperazine-2',5'-dione (94659-47-9) + amoxicillin (2S)-piperazine-2',5'-dione (94659-47-9)

Guidance literature:

In various solvent(s); for 20h; Ambient temperature; pH=9.2;

DOI:10.1248/cpb.34.2239

Downstream raw materials:

amoxicillin (2R)-piperazine-2',5'-dione

amoxicillin (2S)-piperazine-2',5'-dione

6-[2-(4-Hydroxy-phenyl)-2-(5-methyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-acetylamino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

6-[2-(5-Ethyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-2-(4-hydroxy-phenyl)-acetylamino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Refernces