(2S,5R,6R)-6-azaniumyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Base Information

• Chemical Name: (2S,5R,6R)-6-azaniumyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 551-16-6
• Molecular Formula: C8H12N2O3S
• Molecular Weight: 216.261
• Hs Code.: 2941.10
• Mol file: 551-16-6.mol

Synonyms:CHEBI:57869;6-aminopenicillanic acid zwitterion;(2S,5R,6R)-6-azaniumyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;6-azaniumyl-2,2-dimethylpenam-3alpha-carboxylate

Chemical Property of (2S,5R,6R)-6-azaniumyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

• Appearance/Colour: White to cream fine powder
• Vapor Pressure: 9.54E-10mmHg at 25°C
• Melting Point: 198-200 °C (dec.)(lit.)
• Refractive Index: 1.656
• Boiling Point: 460.2 °C at 760 mmHg
• PKA: pKa 2.3 (Uncertain)
• Flash Point: 232.1 °C
• PSA: 108.93000
• Density: 1.52 g/cm³
• LogP: 0.09880
• Storage Temp.: 2-8°C
• Solubility.: 2.46g/l
• Water Solubility.: Soluble in water and hydrochoric acid.
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 216.05686342
• Heavy Atom Count: 14
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

6-APA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-36/37-45-37-24-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)[NH3+])C(=O)[O-])C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)[NH3+])C(=O)[O-])C
• Uses: (+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins. 6-Aminopenicillanic acid is the basic unit in penicillin?s, which is obtained from the fermentation brew of the Penicillium mold. It acts as a starting material for the preparation of many semisynthetic penicillins. Further, it serves as apharmaceutical intermediate. In addition to this, it is used in antibiotics research and experimental application.

Technology Process of (2S,5R,6R)-6-azaniumyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

There total 42 articles about (2S,5R,6R)-6-azaniumyl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 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: 70.5%

→ 6-[D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinocarbonylamino)-p-hydroxyphenylacetamido]penicillanic acid + 6-aminopenicillanic acid (551-16-6,1079-37-4,3115-55-7,21794-93-4,145920-51-0)

Guidance literature:

Reference yield: 59.0%

(2S,5R,6R)-Benzyl 6-Azido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (129096-81-7) → 6-Aminopenicillanic Acid (551-16-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; Ambient temperature;

DOI:10.1021/jo00304a024

Reference yield:

amoxicillin (26787-78-0,81030-75-3) → Thiazole-4-carboxylic acid (3973-08-8) + 5,5-Dimethyl-4,5-dihydro-thiazole-4-carboxylic acid (740742-98-7) + formic acid (64-18-6) + glycolic Acid (79-14-1) + 1,5-pentanedioic acid (110-94-1) + Adipic acid (124-04-9) + tartronic acid (80-69-3) + glyceric acid (473-81-4,118916-26-0) + oxamic acid (471-47-6) + succinic acid (110-15-6) + C5H8O6S (1378848-02-2) + pisolithin A (15573-67-8) + C9H10N2O4 + C9H12N2O5S + C8H10N2O6S + C9H14N2O7S + C9H12N2O6S + C8H10N2O4S + C10H12N2O7S + C15H21N3O4S (1356020-01-3,57414-05-8) + C15H18N2O4S + C14H21N3O3S + C8H12N2O4S + C8H10N2O5S + C6H10O7S + C6H7NO4S + C6H11NO3S + C6H9NO3S + oxalic acid (144-62-7,97993-78-7) + acetic acid (64-19-7,77671-22-8) + propionic acid (802294-64-0,79-09-4) + 2-oxo-propionic acid (127-17-3) + tartaric acid (87-69-4,138508-61-9) + 6-aminopenicillanic acid (551-16-6) + benzoic acid (65-85-0,8013-63-6) + Glyoxilic acid (298-12-4) + 2-hydroxy-3-(4-hydroxyphenyl)pyrazine + 2-butenedioic acid (6915-18-0,26099-09-2) + butyric acid (107-92-6) + (4S)-2t-{(R)-[(R)-2-amino-2-(4-hydroxy-phenyl)-acetylamino]-carboxy-methyl}-5,5-dimethyl-thiazolidine-4r-carboxylic acid (57457-65-5) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With Ru/CNT; sodium hydroxide; for 8h; Reagent/catalyst; Electrolysis;

DOI:10.1016/j.cattod.2019.06.039

upstream raw materials:

penicillin G

6R(β)-tritylaminopenicillanic acid

Penicillin G potassium

6β-(3-oxo-3H-isobenzofuran-1-ylideneamino)-penicillanic acid

Downstream raw materials:

6R(β)-tritylaminopenicillanic acid

Refernces

• 1、 Zhaoyu, Zheng,Ping, Xue,Keren, Shi,Weiwei, Zhang,Chunmiao, Hu,Peng, Li. "Di-functional magnetic nanoflowers: A highly efficient support for immobilizing penicillin G acylase". . p. 1591 - 1601. Retrieved 2020.
• 2、 Ferreira, Marta,Kuzniarska-Biernacka, Iwona,Fonseca, António M.,Neves, Isabel C.,Soares, Olívia S.G.P.,Pereira, Manuel F.R.,Figueiredo, José L.,Parpot, Pier. "Electrochemical oxidation of amoxicillin on carbon nanotubes and carbon nanotube supported metal modified electrodes". . p. 322 - 331. Retrieved 2019/07/10.
• 3、 -. "A PROCESS FOR THE PREPARATION OF AMOXICILLIN TRIHYDRATE". Page/Page column 11; 12. . Retrieved 2014/09/03.