C6-(N1-methyl-1,2,3-trazolylmethylene)penem

Base Information

• Chemical Name: C6-(N1-methyl-1,2,3-trazolylmethylene)penem
• CAS No.: 102209-75-6
• Molecular Formula: C10H8 N4 O3 S . Na
• Molecular Weight: 286.246

Synonyms:4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-[(1-methyl-1H-1,2,3-triazol-4-yl)methylene]-7-oxo-, sodium salt,(5R,6Z)- (9CI); 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-[(1-methyl-1H-1,2,3-triazol-4-yl)methylene]-7-oxo-, sodium salt, [R-(Z)]-;1H-1,2,3-Triazole, 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidderiv.; BRL 42715

Chemical Property of C6-(N1-methyl-1,2,3-trazolylmethylene)penem

Chemical Property:

• Vapor Pressure: 1.19E-19mmHg at 25°C
• Boiling Point: 649.5°Cat760mmHg
• Flash Point: 346.6°C
• PSA: 116.45000
• Density: g/cm³
• LogP: -1.35720

Purity/Quality:

99% ^*data from raw suppliers

C6-(N1-METHYL-1,2,3-TRAZOLYLMETHYLENE)PENEM 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of C6-(N1-methyl-1,2,3-trazolylmethylene)penem

There total 10 articles about C6-(N1-methyl-1,2,3-trazolylmethylene)penem 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: 75.0%

p-methoxybenzyl (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylate (114409-04-0) → (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid sodium salt (102209-75-6)

Guidance literature:

With disodium hydrogenphosphate; aluminium trichloride; methoxybenzene; In dichloromethane; -40 deg C, 10 min then -40 deg C to 20 deg C, 10 min;

DOI:10.1039/c39890000371

Reference yield:

p-methoxybenzyl-6-α-bromopenicillanate (96572-55-3) → (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid sodium salt (102209-75-6)

Guidance literature:

Multi-step reaction with 10 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / 5 °C

2: toluene / Heating

3: toluene / Heating

4: Et₃N / toluene / 2 h / 5 °C

5: NaI, 4-N,N-dimethylaminopyridine, PPh₃ / acetonitrile / -20 deg C, 30 min then 5 deg C, 45 min

6: O₃ / ethyl acetate / 1 h / -78 °C

7: trimethyl phosphite / toluene / 30 h / 95 °C

8: 1.) lithium diphenylamide / 1.) THF, -78 deg C, 1 min; 2.) THF, -78 deg C to 20 deg C, 10 min

9: Zn, N,N,N',N'-tetramethylethylenediamine dihydrochloride, ammonium chloride / dimethylformamide / 1 h / 20 °C

10: 75 percent / AlCl₃, anisole, Na₂HPO₄ / CH₂Cl₂ / -40 deg C, 10 min then -40 deg C to 20 deg C, 10 min

With dmap; disodium hydrogenphosphate; aluminium trichloride; ammonium chloride; N, N, N', N'-tetramethylethylendiammonium dichloride; lithium diphenylamide; ozone; methoxybenzene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; zinc; phosphorous acid trimethyl ester; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/c39890000371

Reference yield:

p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (114409-16-4) → (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid sodium salt (102209-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium diphenylamide / 1.) THF, -78 deg C, 1 min; 2.) THF, -78 deg C to 20 deg C, 10 min

2: Zn, N,N,N',N'-tetramethylethylenediamine dihydrochloride, ammonium chloride / dimethylformamide / 1 h / 20 °C

3: 75 percent / AlCl₃, anisole, Na₂HPO₄ / CH₂Cl₂ / -40 deg C, 10 min then -40 deg C to 20 deg C, 10 min

With disodium hydrogenphosphate; aluminium trichloride; ammonium chloride; N, N, N', N'-tetramethylethylendiammonium dichloride; lithium diphenylamide; methoxybenzene; zinc; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c39890000371

upstream raw materials:

p-methoxybenzyl (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylate

p-methoxybenzyl-6-α-bromopenicillanate

p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

p-methoxybenzyl 2-<(3S,4R)-3-bromo-4-formylthio-2-oxoazetidin-1-yl>-2-oxoacetate

Downstream raw materials:

stavudin

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