(6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

Base Information

• Chemical Name: (6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester
• CAS No.: 114019-02-2
• Molecular Formula: C₁₁H₁₄N₂O₄
• Molecular Weight: 238.243
• Mol file: 114019-02-2.mol

Synonyms:(6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

Chemical Property of (6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

There total 1 articles about (6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl 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:

allyl bromoacetate (40630-84-0) → (6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester (114019-02-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 59 percent / tetrabutylammonium bromide, KOH / tetrahydrofuran / 20 h

2: 87 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C

3: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran

4: 95 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran

5: 1.) p-toluenesulfonic acid monohydrate, 2.) sodium bicarbonate, pH 8 / 1.) acetone, 19 h, 2.) EtOAc, H₂O

With potassium hydroxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jm00401a020

Reference yield:

(6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester (114019-02-2) → (6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-methyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid (113600-01-4)

Guidance literature:

Multi-step reaction with 2 steps

1: EEDQ / ethyl acetate / 3 h / Ambient temperature

2: 44 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾, PPh₃, 2-ethylhexanoic acid / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-Ethylhexanoic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triphenylphosphine; In dichloromethane; ethyl acetate;

DOI:10.1021/jm00401a020

Reference yield:

(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine (84792-41-6) + (6S,7S)-7-Amino-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester (114019-02-2) → (6S,7S)-7-[(R)-2-Allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester (113599-87-4)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In ethyl acetate; for 3h; Yield given; Ambient temperature;

DOI:10.1021/jm00401a020

upstream raw materials:

allyl bromoacetate

Downstream raw materials:

(6S,7S)-7-[(R)-2-Allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

(6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-methyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid