Benzylpenillic acid

Base Information

• Chemical Name: Benzylpenillic acid
• CAS No.: 13093-87-3
• Molecular Formula: C16H18N2O4S
• Molecular Weight: 334.396
• NSC Number: 76064
• DSSTox Substance ID: DTXSID80291510
• Nikkaji Number: J866.543E
• ChEMBL ID: CHEMBL1733416
• Mol file: 13093-87-3.mol

Synonyms:Benzylpenillic acid;13093-87-3;NSC76064;5-benzyl-2,2-dimethyl-2,3,7,7a-tetrahydroimidazo[5,1-b][1,3]thiazole-3,7-dicarboxylic acid;MLS002693971;5-benzyl-2,2-dimethyl-7,7a-dihydro-3H-imidazo[5,1-b][1,3]thiazole-3,7-dicarboxylic acid;5-Benzyl-2,2-dimethyl-2,3,7,7a-tetrahydroimidazo[5,1-b]thiazole-3,7-dicarboxylic acid;NSC-76064;CHEMBL1733416;DTXSID80291510;HMS3094O13;Benzylpenicillin EP(CP) Impurity D;NCI60_041676;SMR001559906;5-Benzyl-2,2-dimethyl-2,3,7,7a-tetrahydroimidazo[5,1-b]thiazole-3,7-dicarboxylicacid;Imidazo[5,7-dicarboxylic acid, 2,3,7,7a-tetrahydro-2,2-dimethyl-5-(phenylmethyl)-;Imidazo[5,7-dicarboxylic acid, 5-benzyl-2,3,7,7a-tetrahydro-2,2-dimethyl-

Chemical Property of Benzylpenillic acid

Chemical Property:

• Vapor Pressure: 3E-16mmHg at 25°C
• Boiling Point: 620.3°Cat760mmHg
• Flash Point: 329°C
• Density: 1.47g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 334.09872823
• Heavy Atom Count: 23
• Complexity: 542

Purity/Quality:

≧95%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(N=C2CC3=CC=CC=C3)C(=O)O)C(=O)O)C

Technology Process of Benzylpenillic acid

There total 12 articles about Benzylpenillic 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: 23.0%

6-(2-phenylacetamido)penicillanic acid (61-33-6,7005-30-3,30411-69-9,47294-41-7,47294-44-0,70019-71-5) → benzylpenicilloic acid (13057-98-2) + benzylpenicillenic acid (3264-88-8,32347-08-3,108101-71-9) + benzylpenicillic acid (13093-87-3)

Guidance literature:

Rate constant; acidic degradation;

Reference yield:

penicillin G (61-33-6) → benzylpenicilloic acid (13057-98-2,87492-68-0,89014-19-7,96572-86-0,96572-87-1) + benzylpenamaldic acid (64950-15-8,108101-72-0) + benzylpenilloic acid (501-34-8,28325-47-5) + benzylpenicillenic acid (3264-88-8,32347-08-3,108101-71-9) + benzylpenicillic acid (13093-87-3)

Guidance literature:

With hydrogenchloride; In water; at 30 ℃; Rate constant; hydrolysis;

Reference yield:

3,3-dimethyl-D-cysteine (52-67-5) + 2-Benzyl-4-[1-methoxy-meth-(E)-ylidene]-4H-oxazol-5-one (1212-44-8) → (3S,7Ξ,7aΞ)-5-benzyl-2,2-dimethyl-2,3,7,7a-tetrahydro-imidazo[5,1-b]thiazole-3,7-dicarboxylic acid (13093-87-3)

Guidance literature:

With pyridine; triethylamine;

DOI:10.1126/science.108.2797.136

upstream raw materials:

3,3-dimethyl-D-cysteine

2-Benzyl-4-[1-methoxy-meth-(E)-ylidene]-4H-oxazol-5-one

L-(+)-penicillamine hydrochloride

penicillamine hydrochloride

Downstream raw materials:

benzylpenilloic acid

Refernces

• 1、 Kessler, David P.,Cushman, Mark,Ghebre-Sellassie, Isaac,Knevel, Adelbert M.,Hem, Stanley L.. "Investigation of a Proposed Penicillin G Acidic Degradation Scheme using High-pressure Liquid Chromatography and Optimization Techniques and Mechanistic Considerations". . p. 1699 - 1704. Retrieved 2007/10/02.