benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Base Information

• Chemical Name: benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 180199-68-2
• Molecular Formula: C₂₅H₂₆N₂O₅S
• Molecular Weight: 466.558
• Mol file: 180199-68-2.mol

Synonyms:benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Chemical Property of benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

There total 7 articles about benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[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: 80.0%

N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide (129986-67-0) + diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (162514-95-6) → benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (180199-68-2)

Guidance literature:

With lithium perchlorate; In acetonitrile; at -20 ℃; for 4h;

DOI:10.1021/jm9601967

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (180199-68-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaNO₂, H⁺, KBr, 2.) CH₃CO₃H

2: 90 percent / PBu₃ / methanol / 0.75 h / Ambient temperature

3: 84.2 percent / Heating

4: 1.) AcOAg, 2.) thiourea, pyridine / 1.) CH₂Cl₂, 6 h, 2.) DMF, from 0 deg C to RT

5: 1.) oxalyl chloride, DMSO, 2.) TEA / 1.) CH₂Cl₂, -70 deg C, 3 h, 2.) CH₂Cl₂, from -70 deg C to -10 deg C, 20 min

6: 80 percent / LiClO₄ / acetonitrile / 4 h / -20 °C

With pyridine; peracetic acid; oxalyl dichloride; tributylphosphine; TEA; silver(I) acetate; lithium perchlorate; hydrogen cation; dimethyl sulfoxide; thiourea; potassium bromide; sodium nitrite; In methanol; acetonitrile;

DOI:10.1021/jm9601967

Reference yield:

benzophenone hydrazone (5350-57-2) → benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate (180199-68-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaNO₂, H⁺, KBr, 2.) CH₃CO₃H

2: 90 percent / PBu₃ / methanol / 0.75 h / Ambient temperature

3: 84.2 percent / Heating

4: 1.) AcOAg, 2.) thiourea, pyridine / 1.) CH₂Cl₂, 6 h, 2.) DMF, from 0 deg C to RT

5: 1.) oxalyl chloride, DMSO, 2.) TEA / 1.) CH₂Cl₂, -70 deg C, 3 h, 2.) CH₂Cl₂, from -70 deg C to -10 deg C, 20 min

6: 80 percent / LiClO₄ / acetonitrile / 4 h / -20 °C

With pyridine; peracetic acid; oxalyl dichloride; tributylphosphine; TEA; silver(I) acetate; lithium perchlorate; hydrogen cation; dimethyl sulfoxide; thiourea; potassium bromide; sodium nitrite; In methanol; acetonitrile;

DOI:10.1021/jm9601967

upstream raw materials:

N-methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide

diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

6-Aminopenicillanic Acid

benzophenone hydrazone

Downstream raw materials:

Benzhydryl (E)-(2S,3S,5R)-3-[2-(methoxy-methyl-carbamoyl)-vinyl]-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate