(5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Base Information

• Chemical Name: (5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester
• CAS No.: 623565-08-2
• Molecular Formula: C₂₂H₁₉BrN₄O₉S₂
• Molecular Weight: 627.45

Synonyms:(5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Chemical Property of (5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

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Technology Process of (5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

There total 6 articles about (5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl 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: 22.0%

5,5-dioxo-4,5,6,7-tetrahydro-5λ6-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde (623565-07-1) + acetic anhydride (108-24-7) → (5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ6-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623565-08-2)

Guidance literature:

5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde; (5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester; With triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile; at -20 ℃; for 3h;

acetic anhydride; With dmap; In tetrahydrofuran; acetonitrile; at -20 - 0 ℃; for 16h;

Reference yield: 22.0%

5,5-dioxo-4,5,6,7-tetrahydro-5λ6-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde (623565-07-1) + acetic anhydride (108-24-7) + (5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623564-16-9) → (5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ6-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623565-08-2)

Guidance literature:

5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde; (5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester; With triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile; at -20 ℃; for 3h;

acetic anhydride; With dmap; In tetrahydrofuran; acetonitrile; at 0 ℃;

DOI:10.1021/jm060021p

Reference yield:

5,5-Dioxo-4,5,6,7-tetrahydro-5α6-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde + (5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623564-16-9) → (5R,6RS)-6-[(RS)-acetoxy-(5,5-dioxo-4,5,6,7-tetrahydro-5λ6-pyrazolo[5,1-c][1,4]thiazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester (623565-08-2)

Guidance literature:

With acetic anhydride; In acetonitrile;

upstream raw materials:

5,5-dioxo-4,5,6,7-tetrahydro-5λ⁶-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde

acetic anhydride

(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde

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