(4-Nitrophenyl)methyl (4S,5R,6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

• Chemical Name: (4-Nitrophenyl)methyl (4S,5R,6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS No.: 189188-38-3
• Molecular Formula: C₂₉H₂₇N₂O₁₀P
• Molecular Weight: 594.515
• UNII: 6P38GC95JV
• Nikkaji Number: J1.817.972E
• Mol file: 189188-38-3.mol

Synonyms:189188-38-3;(4-Nitrophenyl)methyl (4S,5R,6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;6P38GC95JV;SCHEMBL10013148;(4-Nitrophenyl)methyl (4S,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;(4S,5R,6S)-4-Nitrobenzyl 3-((diphenoxyphosphoryl)oxy)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;(4S,5R,6S)-4-Nitrobenzyl3-((diphenoxyphosphoryl)oxy)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, [4S-[4alpha,5alpha,6alpha(S*)]]-;1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4S,5R,6S)-;4-Nitrobenzyl (4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]- 4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property of (4-Nitrophenyl)methyl (4S,5R,6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property:

• Boiling Point: 722.4±60.0 °C(Predicted)
• PKA: 14.36±0.20(Predicted)
• Density: 1.47±0.1 g/cm3(Predicted)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 594.14033206
• Heavy Atom Count: 42
• Complexity: 1060

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrobenzyl(4S,5R,6S)-3-[(diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C2C(C(=O)N2C(=C1OP(=O)(OC3=CC=CC=C3)OC4=CC=CC=C4)C(=O)OCC5=CC=C(C=C5)[N+](=O)[O-])C(C)O
• Isomeric SMILES: C[C@H]1[C@@H]2[C@H](C(=O)N2C(=C1OP(=O)(OC3=CC=CC=C3)OC4=CC=CC=C4)C(=O)OCC5=CC=C(C=C5)[N+](=O)[O-])[C@@H](C)O
• Uses: 4-Nitrobenzyl (4S,5R,6S)-3-[(Diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]- 4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 4-Nitrobenzyl (4S,5R,6S)-3-[(Diphenylphosphono)oxy]-6-[(R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate is an intermediate for the production of the Carbapenem antibiotic. It is also an Meropenem intermediate, an injectable antibiotic used to treat a wide variety of infections.

Technology Process of (4-Nitrophenyl)methyl (4S,5R,6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 26 articles about (4-Nitrophenyl)methyl (4S,5R,6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 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: 81.0%

4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate (104873-15-6) + chlorophosphoric acid diphenyl ester (2524-64-3) → (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (93711-81-0,90776-59-3,189188-38-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at -15 - -10 ℃; for 5h;

Reference yield:

C17H18N2O7 + chlorophosphoric acid diphenyl ester (2524-64-3) → (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (93711-81-0,90776-59-3,189188-38-3)

Guidance literature:

C₁₇H₁₈N₂O₇; chlorophosphoric acid diphenyl ester; With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - -5 ℃;

With hydrogenchloride; In dichloromethane; at -5 - 15 ℃;

Reference yield:

magnesium 4-nitrobenzyl malonate (105995-50-4) → (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (93711-81-0,90776-59-3,189188-38-3)

Guidance literature:

Multi-step reaction with 6 steps

1: dichloromethane / 3 h / 20 - 45 °C / Reflux

2: triethylamine; 4-toluenesulfonyl azide / dichloromethane / 2 h / 20 - 30 °C

3: hydrogenchloride; methanol / dichloromethane; water / 3 h / 20 - 30 °C

4: dichloromethane; Isopropyl acetate / 25 - 30 °C

5: zinc dibromide; rhodium (II) octanoate dimer / dichloromethane / 40 °C / Reflux

6: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 0 °C

With hydrogenchloride; methanol; dmap; 4-toluenesulfonyl azide; rhodium (II) octanoate dimer; triethylamine; N-ethyl-N,N-diisopropylamine; zinc dibromide; In dichloromethane; Isopropyl acetate; water;

upstream raw materials:

(2R,4R,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

chlorophosphoric acid diphenyl ester

(R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid

Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester

Downstream raw materials:

(4R,5S,6S)-3-[(3S,5S)-5-(2-Carbamoyl-ethylsulfanylmethyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF MEROPENEM". Page/Page column 10-12. . Retrieved 2011/12/02.
• 2、 -. "PROCESS FOR THE PREPARATION OF CARBAPENEM COMPOUNDS". Page/Page column 21-23. . Retrieved 2010/04/03.