benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide

Base Information

• Chemical Name: benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide
• CAS No.: 93521-41-6
• Molecular Formula: C₃₅H₃₈N₆O₁₃S
• Molecular Weight: 782.785
• Mol file: 93521-41-6.mol

Synonyms:

Chemical Property of benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide

There total 5 articles about benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-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: 21.0%

benzyl 6β-amino-6α-formamidopenicillanate 1α-oxide (121054-10-2) + (D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetic acid (86061-90-7) → benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide (93521-41-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; 1) 0 deg C 2) RT, 1 h;

Reference yield:

(2S,5R,6R)-6-{(R)-2-(3,4-Diacetoxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-acetylamino}-6-formylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (86061-93-0) → benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide (93521-41-6) + benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1β-oxide (93521-40-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2h; Yield given. Yields of byproduct given;

Reference yield:

benzyl 6β-(N-trifluoromethylsulphonylamino)penicillanate (82954-45-8) → benzyl 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide (93521-41-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

2: 83 percent / 5.24percent peracetic acid in AcOH / CH₂Cl₂ / 1) -10 deg C 2) 0 deg C, 16 h

3: 89 percent / zinc powder, 1M HCl, 1M potassium hydrogen phosphate / tetrahydrofuran; H₂O / pH= 4-6

4: 21 percent / DCC / CH₂Cl₂ / 1) 0 deg C 2) RT, 1 h

With hydrogenchloride; peracetic acid; dmap; dipotassium hydrogenphosphate; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

benzyl 6β-amino-6α-formamidopenicillanate 1α-oxide

(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetic acid

(2S,5R,6R)-6-{(R)-2-(3,4-Diacetoxy-phenyl)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-acetylamino}-6-formylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

benzyl 6β-(N-trifluoromethylsulphonylamino)penicillanate

Downstream raw materials:

sodium 6β-<(D)-2-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)-2-(3,4-diacetoxyphenyl)acetamido>-6α-formamidopenicillanate 1α-oxide