3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone

Base Information

• Chemical Name: 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone
• CAS No.: 98269-63-7
• Molecular Formula: C₁₇H₁₅BrN₄O₆
• Molecular Weight: 451.233
• Mol file: 98269-63-7.mol

Synonyms:3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone

Chemical Property of 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone

There total 2 articles about 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 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:

4-nitrobenzyl 2-diazo-3-oxo-butanoate (82551-63-1) → 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone (98269-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / triethylamine / CCl₄ / Ambient temperature

2: 1.) NBS, AIBN, 2.) Me₃SiOTf / 1.) CCl₄, reflux, 30 min, 2.) CH₂Cl₂, -78 deg C, 15 min

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; triethylamine; In tetrachloromethane;

DOI:10.1021/jo00222a012

Reference yield:

p-nitrobenzyl 2-diazo-3-(trimethylsilyl)oxy-3-butenoate (93788-47-7) + 4-acetoxy-3-(1-methylethylidene)-1-(trimethylsilyl)-2-azetidinone (98269-60-4) → 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone (98269-63-7) + 3-<(Z)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; Yield given. Multistep reaction. Yields of byproduct given; 1.) CCl₄, reflux, 30 min, 2.) CH₂Cl₂, -78 deg C, 15 min;

DOI:10.1021/jo00222a012

Reference yield: 81.0%

3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone (98269-63-7) → p-nitrobenzyl 6-<(E)-2-bromo-1-methylethylidene>-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:

With dirhodium tetraacetate; In benzene; for 0.5h; Heating;

DOI:10.1021/jo00222a012

upstream raw materials:

p-nitrobenzyl 2-diazo-3-(trimethylsilyl)oxy-3-butenoate

4-acetoxy-3-(1-methylethylidene)-1-(trimethylsilyl)-2-azetidinone

4-nitrobenzyl 2-diazo-3-oxo-butanoate