benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide

Base Information

• Chemical Name: benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide
• CAS No.: 205320-23-6
• Molecular Formula: C₂₁H₂₁NO₄S
• Molecular Weight: 383.468
• Mol file: 205320-23-6.mol

Synonyms:benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide

Chemical Property of benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide

There total 3 articles about benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide 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: 96.0%

Benzhydryl 6α-bromopenicillanate-1-oxide (80353-26-0,100349-41-5) → benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide (205320-23-6)

Guidance literature:

With acetic acid; zinc; In acetonitrile; at 0 ℃; for 3h;

DOI:10.1055/s-1986-31587

Reference yield:

6-aminopenicillanic acid (551-16-6,1079-37-4,3115-55-7,21794-93-4,145920-51-0) → benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide (205320-23-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / 2.5N H₂SO₄, KBr, NaNO₂ / ethanol; H₂O / 3.5 h / 6 - 8 °C

2: 1.) peracetic acid, 2.) 1percent aq. KI, 10percent aq. H₂SO₄, peracetic acid / 1.) H₂O, CHCl₃, 0 deg C, 30 min, 2.) 0 deg C, 1 h; r.t., 1 h

3: 96 percent / Zn, glacial acetic acid / acetonitrile / 3 h / 0 °C

With peracetic acid; sulfuric acid; acetic acid; potassium iodide; potassium bromide; zinc; sodium nitrite; In ethanol; water; acetonitrile;

DOI:10.1055/s-1986-31587

Reference yield:

6α-Bromopenicillanic acid (205320-26-9) → benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide (205320-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) peracetic acid, 2.) 1percent aq. KI, 10percent aq. H₂SO₄, peracetic acid / 1.) H₂O, CHCl₃, 0 deg C, 30 min, 2.) 0 deg C, 1 h; r.t., 1 h

2: 96 percent / Zn, glacial acetic acid / acetonitrile / 3 h / 0 °C

With peracetic acid; sulfuric acid; acetic acid; potassium iodide; zinc; In acetonitrile;

DOI:10.1055/s-1986-31587

upstream raw materials:

Benzhydryl 6α-bromopenicillanate-1-oxide

6-aminopenicillanic acid

6α-Bromopenicillanic acid

Downstream raw materials:

(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester

tazobactam acid

2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester

Benzhydryl 2β-bromomethyl-2α-methyl-6,6-dihydropenicillanate