3-Acetoxymethyl-7-methoxy-1-aza-5-thia-8-oxo-bicyclo(4.2.0)oct-2-ene-2-carboxypyrrolidine carboxamide

Base Information

• Chemical Name: 3-Acetoxymethyl-7-methoxy-1-aza-5-thia-8-oxo-bicyclo(4.2.0)oct-2-ene-2-carboxypyrrolidine carboxamide
• CAS No.: 116507-04-1
• Molecular Formula: C₁₆H₂₀N₂O₉S
• Molecular Weight: 416.409
• UNII: YMN4MD1ZGQ
• DSSTox Substance ID: DTXSID30922084
• Nikkaji Number: J423.989J
• Wikidata: Q76010314
• Pharos Ligand ID: W73FLRLVU66L
• ChEMBL ID: CHEMBL446371
• Mol file: 116507-04-1.mol

Synonyms:3-acetoxymethyl-7-methoxy-1-aza-5-thia-8-oxo-bicyclo(4.2.0)oct-2-ene-2-carboxypyrrolidine carboxamide;L 658,758;L 658758;L-658,758;L-658758

Chemical Property of 3-Acetoxymethyl-7-methoxy-1-aza-5-thia-8-oxo-bicyclo(4.2.0)oct-2-ene-2-carboxypyrrolidine carboxamide

Chemical Property:

• Vapor Pressure: 1.12E-28mmHg at 25°C
• Boiling Point: 807.8°C at 760 mmHg
• Flash Point: 442.3°C
• Density: 1.59g/cm³
• XLogP3: -2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 416.08895139
• Heavy Atom Count: 28
• Complexity: 873

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)OC)S(=O)(=O)C1)C(=O)N3CCCC3C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@H](C2=O)OC)S(=O)(=O)C1)C(=O)N3CCC[C@H]3C(=O)O

Technology Process of 3-Acetoxymethyl-7-methoxy-1-aza-5-thia-8-oxo-bicyclo(4.2.0)oct-2-ene-2-carboxypyrrolidine carboxamide

There total 7 articles about 3-Acetoxymethyl-7-methoxy-1-aza-5-thia-8-oxo-bicyclo(4.2.0)oct-2-ene-2-carboxypyrrolidine carboxamide 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: 97.0%

3-(acetoxymethyl)-2-<<2(S)-(tert-butoxycarbonyl)pyrrolidino>carbonyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene 5,5-dioxide (116536-19-7) → L 658758 (116507-04-1)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; at 0 ℃; for 1h;

DOI:10.1021/jm00099a002

Reference yield:

3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (95570-59-5) → L 658758 (116507-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexylcarbodiimide / dimethylformamide / 1.5 h / Ambient temperature

2: 2.) m-chloroperbenzoic acid, 3.) pyridine

3: 97 percent / trifluoroacetic acid, anisole / 1 h / 0 °C

With pyridine; methoxybenzene; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm00099a002

Reference yield:

3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid 5,5-dioxide (104164-02-5) → L 658758 (116507-04-1)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 15 - 20 °C

2: 86 percent / triethylamine / CH₂Cl₂ / 0.25 h / -15 - 25 °C

3: 97 percent / trifluoroacetic acid, anisole / 1 h / 0 °C

With oxalyl dichloride; methoxybenzene; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm00099a002

upstream raw materials:

3-(acetoxymethyl)-2-<<2(S)-(tert-butoxycarbonyl)pyrrolidino>carbonyl>-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene 5,5-dioxide

3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid 5,5-dioxide

t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate

Refernces