(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
• General Description: 6-Aminopenicillanic acid (6-APA) is a key intermediate in the synthesis of penicillin derivatives, produced through a stereocontrolled total synthesis involving nitroalkene cyclization strategies. The compound is derived from (R,R)-tartaric acid, with critical steps including the reaction of nitroalkenes with tetrabutylammonium fluoride, followed by ozone and DBU treatment to form bicyclic β-lactams, which are subsequently converted into 6-APA. This method highlights the utility of (benzyloxy)nitromethane in β-lactam chemistry and demonstrates an efficient approach for constructing functionalized β-lactam systems.

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:

methyl 6β-(triphenylmethylamino)penicillinate

penicillin G

6β-[(Ξ)-2-(2,4-dichloro-phenoxy)-propionylamino]-penicillanic acid

6β-(4-dichloromethyl-benzoylamino)-penicillanic acid

Refernces

Total syntheses of penicillanic acid s,s-dioxide and 6-aminopenicillanic acid using(benzyloxy)nitromethane

10.1021/jo00304a024

The research focuses on the stereocontrolled total syntheses of penicillanic acid S,S-dioxide (10) and 6-aminopenicillanic acid (26) derived from (S)-aspartic acid and (R,R)-tartaric acid, respectively. The study's key steps involve the preparation and cyclization of nitroalkenes 8 and 23, with the reaction of these compounds with tetrabutylammonium fluoride followed by ozone and DBU yielding the bicyclic P-lactams 9 and 24, which are then transformed into the target penicillanic acid derivatives 10 and 26. The research concludes that (benzyloxy)nitromethane is a highly useful reagent in β-lactam chemistry, and the nitroalkene ring closure strategy is efficient and effective for preparing polyfunctional bicyclic β-lactams, with potential general applicability for constructing novel β-lactam systems.