p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• CAS No.: 156662-53-2
• Molecular Formula: C₂₅H₁₆N₆O₁₀S₂
• Molecular Weight: 624.568
• Mol file: 156662-53-2.mol

Synonyms:p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property of p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

There total 7 articles about p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-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: 98.0%

2-mercapto-1,3,4-thiadiazole (18686-82-3) + p-nitrobenzyl (6S,7S)-3-bromomethyl-7-(4-nitrophthalimido)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (156662-52-1) → p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (156662-53-2)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1016/S0957-4166(00)86216-3

Reference yield:

(2R,3S)-2-[(2S,3S)-2-Formyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester (1026269-90-8) → p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (156662-53-2)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium borohydride, boron trifluoride etherate / tetrahydrofuran / 1 h / 0 °C

2: pyridine / 6 h / -15 °C

3: CrO₃, conc. sulfuric acid / acetonitrile; H₂O / 0.67 h

4: 1.) bromine, 2.) aq. sodium bicarbonate / 1.) dioxane, 40 deg C, 2 h, 2.) dioxane, 30 deg C, 1 h

5: 98 percent / triethylamine / dimethylformamide / 1 h / 0 °C

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sulfuric acid; boron trifluoride diethyl etherate; bromine; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(00)86216-3

Reference yield:

(2R,3S)-3-Hydroxy-2-[(2S,3S)-2-hydroxymethyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-butyric acid 4-nitro-benzyl ester (133622-35-2) → p-nitrobenzyl (6S,7S)-7-(4-nitrophthalimido)-8-oxo-3-<(1,3,4-thiadiazol-2-yl)thiomethyl>-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (156662-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 6 h / -15 °C

2: CrO₃, conc. sulfuric acid / acetonitrile; H₂O / 0.67 h

3: 1.) bromine, 2.) aq. sodium bicarbonate / 1.) dioxane, 40 deg C, 2 h, 2.) dioxane, 30 deg C, 1 h

4: 98 percent / triethylamine / dimethylformamide / 1 h / 0 °C

With pyridine; chromium(VI) oxide; sulfuric acid; bromine; sodium hydrogencarbonate; triethylamine; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(00)86216-3

upstream raw materials:

2-mercapto-1,3,4-thiadiazole

p-nitrobenzyl (6S,7S)-3-bromomethyl-7-(4-nitrophthalimido)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

(2R,3S)-2-[(2S,3S)-2-Formyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-3-hydroxy-butyric acid 4-nitro-benzyl ester

(2R,3S)-3-Hydroxy-2-[(2S,3S)-2-hydroxymethyl-3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-butyric acid 4-nitro-benzyl ester