(F-9 (M-6))

Base Information

• Chemical Name: (F-9 (M-6))
• CAS No.: 90822-24-5
• Molecular Formula: C29H27N2O10P
• Molecular Weight: 390.353
• Mol file: 90822-24-5.mol

Synonyms:2-Azetidinebutanoic acid, α-diazo-3-(1-hydroxyethyl)-γ-methyl-β,4-dioxo-, (4-nitrophenyl)methyl ester, [2R-[2α(R*),3β(R*)]]-;(R)-4-nitrobenzyl 2-diazo-4-((2R,3S)-3-((R)-1-hydroxyethyl)-4-oxoazetidin-2-yl)-3-oxopentanoate;2-Azetidinebutanoic acid, α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-, (4-nitrophenyl)methyl ester, (γR,2R,3S)-;

Chemical Property of (F-9 (M-6))

Chemical Property:

• PSA: 175.91000
• LogP: 0.94246

Purity/Quality:

99.9% by HPLC ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Nitrobenzyl (R)-2-diazo-4-((2R,3S)-3-((R)-1-hydroxyethyl)-4-oxoazetidin-2-yl)-3-oxopentanoate is used as a reactant in the preparation of carbapenem compounds for treatment of bacterial infections. It is also the impurity of Meropenem (M225668), which is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia.

Technology Process of (F-9 (M-6))

There total 15 articles about (F-9 (M-6)) 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: 95.0%

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one (90822-23-4) → (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester (90822-24-5)

Guidance literature:

With dodecylbenzenesulfonyl azide; triethylamine; In hexane; acetonitrile; for 3h; Ambient temperature;

Reference yield:

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one (90822-22-3) → (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester (90822-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 6 N aq. HCl / methanol / 2 h / Ambient temperature

2: 95 percent / dodecylbenzenesulfonyl azide, Et₃N / acetonitrile; hexane / 3 h / Ambient temperature

With hydrogenchloride; dodecylbenzenesulfonyl azide; triethylamine; In methanol; hexane; acetonitrile;

Reference yield:

magnesium 4-nitrobenzyl malonate (105995-50-4) → (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester (90822-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / 60 °C

2: 95 percent / conc. HCl / methanol / 1 h / Ambient temperature

3: 90 percent / dodecylbenzenesulfonyl azide, Et₃N / acetonitrile / Ambient temperature

With hydrogenchloride; dodecylbenzenesulfonyl azide; triethylamine; In methanol; acetonitrile;

DOI:10.1021/jo00041a033

upstream raw materials:

(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

(3S,4R)-3-<(1S)-1-hydroxyethyl>-4-methoxycarbonylmethyl-azetidin-2-one

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(methoxycarbonyl)methyl>azetidin-2-one

Downstream raw materials:

4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate

4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate

p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate

(R)-2-Diazo-3-oxo-4-[(2R,3S)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-2-yl]-pentanoic acid 4-nitro-benzyl ester