3-({[(6R,7S)-7-methoxy-5,5-dioxido-8-oxo-2-(pyrrolidin-1-ylcarbonyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}sulfanyl)-2-methyl-1,2-dihydro-1,2,4-triazine-5,6-dione

Base Information

• Chemical Name: 3-({[(6R,7S)-7-methoxy-5,5-dioxido-8-oxo-2-(pyrrolidin-1-ylcarbonyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}sulfanyl)-2-methyl-1,2-dihydro-1,2,4-triazine-5,6-dione
• CAS No.: 119742-06-2
• Molecular Formula: C17H21 N5 O7 S2
• Molecular Weight: 471.5079
• Mol file: 119742-06-2.mol

Synonyms:Pyrrolidine,1-[[7-methoxy-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-yl]carbonyl]-,S,S-dioxide, (6R-cis)-; L 659286; Pyrrolidine, 1-[[7-methoxy-5,5-dioxido-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-yl]carbonyl]-,(6R-cis)-

Chemical Property of 3-({[(6R,7S)-7-methoxy-5,5-dioxido-8-oxo-2-(pyrrolidin-1-ylcarbonyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}sulfanyl)-2-methyl-1,2-dihydro-1,2,4-triazine-5,6-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 185.42000
• Density: 1.79g/cm³
• LogP: -0.99450

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-({[(6R,7S)-7-methoxy-5,5-dioxido-8-oxo-2-(pyrrolidin-1-ylcarbonyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}sulfanyl)-2-methyl-1,2-dihydro-1,2,4-triazine-5,6-dione

There total 6 articles about 3-({[(6R,7S)-7-methoxy-5,5-dioxido-8-oxo-2-(pyrrolidin-1-ylcarbonyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}sulfanyl)-2-methyl-1,2-dihydro-1,2,4-triazine-5,6-dione 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: 85.0%

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine (58909-39-0) + 7α-methoxy-8-oxo-2-(pyrrolidinocarbonyl)-3-(chloromethyl)-5-thia-1-azabicyclo<4.2.0>oct-2-ene 5,5-dioxide (143731-84-4) → L-659,286 (119742-06-2)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; for 16h; Ambient temperature;

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-659,286 (119742-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1: dicyclohexylcarbodiimide / dioxane / 0.5 h / Ambient temperature

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

3: 74 percent / titanium isopropoxide / propan-2-ol / 3 h / 50 °C

4: 38 percent / thionyl chloride, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 85 percent / NaHCO₃ / acetone; H₂O / 16 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; thionyl chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1021/jm00099a002

Reference yield:

Acetic acid (6R,7S)-7-methoxy-5,5,8-trioxo-2-(pyrrolidine-1-carbonyl)-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester (128472-86-6) → L-659,286 (119742-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / titanium isopropoxide / propan-2-ol / 3 h / 50 °C

2: 38 percent / thionyl chloride, pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 85 percent / NaHCO₃ / acetone; H₂O / 16 h / Ambient temperature

With pyridine; titanium(IV) isopropylate; thionyl chloride; sodium hydrogencarbonate; In dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1021/jm00099a002

upstream raw materials:

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

7α-methoxy-8-oxo-2-(pyrrolidinocarbonyl)-3-(chloromethyl)-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

Acetic acid (6R,7S)-7-methoxy-5,5,8-trioxo-2-(pyrrolidine-1-carbonyl)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

Refernces