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

Base Information

• Chemical Name: (6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
• CAS No.: 113600-03-6
• Molecular Formula: C₁₈H₁₉N₃O₆
• Molecular Weight: 373.365
• Mol file: 113600-03-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid 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: 37.0%

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-89-6) → (6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid (113600-03-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-Ethylhexanoic acid; triphenylphosphine; In dichloromethane;

DOI:10.1021/jm00401a020

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) → (6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid (113600-03-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / 1N NaOH / diethyl ether; H₂O; dioxane / 1 h / ice bath

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

3: 37 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾, PPh₃, 2-ethylhexanoic acid / CH₂Cl₂

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-Ethylhexanoic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triphenylphosphine; In 1,4-dioxane; diethyl ether; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00401a020

Reference yield:

(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine (84792-41-6) → (6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid (113600-03-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 37 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

upstream raw materials:

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-cyclopropyl-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

D-4-hydroxyphenylglycine

(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine

allyl (6S,7S)-3-cyclopropyl-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate