benzhydryl 6β-(phenylacetamido)penicillanate 1β-oxide

Base Information

• Chemical Name: benzhydryl 6β-(phenylacetamido)penicillanate 1β-oxide
• CAS No.: 37591-56-3
• Molecular Formula: C₂₉H₂₈N₂O₅S
• Molecular Weight: 516.618
• Mol file: 37591-56-3.mol

Synonyms:benzhydryl 6β-(phenylacetamido)penicillanate 1β-oxide

Chemical Property of benzhydryl 6β-(phenylacetamido)penicillanate 1β-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzhydryl 6β-(phenylacetamido)penicillanate 1β-oxide

There total 7 articles about benzhydryl 6β-(phenylacetamido)penicillanate 1β-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: 94.0%

(S)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (66363-41-5,67565-52-0) → (S)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (37591-56-3,51446-87-8,68000-33-9,69780-17-2,73036-93-8,101833-98-1)

Guidance literature:

With formic acid; dihydrogen peroxide; In dichloromethane; at 0 - 5 ℃; for 4h;

DOI:10.1055/s-1989-27194

Reference yield: 63.0%

(2S,4R,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (101760-76-3) → benzyl 6β-(phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxylate 1α-S-oxide (37591-56-3,51446-87-8,68000-33-9,69780-17-2,73036-93-8,101833-98-1)

Guidance literature:

With ammonium acetate; zinc; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00360a030

Reference yield:

sodium phenylacetate (114-70-5) → benzyl 6β-(phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2α-carboxylate 1α-S-oxide (37591-56-3,51446-87-8,68000-33-9,69780-17-2,73036-93-8,101833-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene / 1.5 h / 55 - 60 °C

2: 52 percent / m-chloroperbenzoic acid (MCPBA) / benzene / 0.5 h / Ambient temperature

3: 63 percent / Zn, 1 M aq. AcONH₄ / tetrahydrofuran / 2 h / Ambient temperature

With ammonium acetate; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; toluene; benzene;

DOI:10.1021/jo00360a030

upstream raw materials:

(S)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,4R,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

sodium phenylacetate

(2S,5R,6R)-6-(Bis-phenylacetyl-amino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Downstream raw materials:

(2S,4S,5R,6S)-6-bromo-3,3-dimethyl-4,7-dioxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid benzhydryl ester

(2S,4S,5R)-3,3-dimethyl-4,7-dioxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid benzhydryl ester

benzhydryl 6-diazopenicillanate 1β-oxide

(R)-2-((1S,5R)-3-Benzyl-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzhydryl ester

Refernces

• 1、 Micetich, Ronald G.,Singh, Rajeshwar,Shaw, Chia C.. "Oxidation Studies on β-Lactam Antibiotics. The 6-(Diacylamino)penicillins". . p. 1811 - 1815. Retrieved 2007/10/02.