(2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 162515-54-0
• Molecular Formula: C₂₅H₂₂N₂O₃S₂
• Molecular Weight: 462.593
• Mol file: 162515-54-0.mol

Synonyms:(2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 7 articles about (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 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: 62.0%

thiazol-2-ylmethyltriphenylphosphonium chloride (115754-94-4) + diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (162514-95-6) → (2S,3S,5R)-3-Methyl-7-oxo-3-((Z)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (162515-55-1) + (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (162515-54-0)

Guidance literature:

With ethyloxirane; for 10h; Heating;

DOI:10.1021/jm9601967

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (162515-54-0)

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: 62 percent / 1,2-epoxybutane / 10 h / Heating

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

DOI:10.1021/jm9601967

Reference yield:

benzophenone hydrazone (5350-57-2) → (2S,3S,5R)-3-Methyl-7-oxo-3-((E)-2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (162515-54-0)

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: 62 percent / 1,2-epoxybutane / 10 h / Heating

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

DOI:10.1021/jm9601967

upstream raw materials:

thiazol-2-ylmethyltriphenylphosphonium chloride

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-methyl-4,4,7-trioxo-3-(2-thiazol-2-yl-vinyl)-4-thia-1-aza-bicyclo [3.2.0]heptane-2-carboxylate

Refernces