6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: 6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 1027013-15-5
• Molecular Formula: C₂₂H₁₉BrN₄O₇S₂
• Molecular Weight: 595.451

Synonyms:6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property of 6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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Technology Process of 6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 3 articles about 6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl 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:

6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazine-2-carbaldehyde (623564-62-5) + 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) → 6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (1027013-15-5)

Guidance literature:

6,7-dihydro-4H-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 ℃;

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

DOI:10.1021/jm060021p

Reference yield:

(6,7-dihydro-4H-pyrazolo[5,1-c] [1,4]thiazin-2-yl)methanol (623564-61-4) → 6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (1027013-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1.78 g / MnO₂ / CHCl₃ / 1 h / Heating

2.1: MgBr₂; Et₃N / tetrahydrofuran; acetonitrile / -20 °C

2.2: tetrahydrofuran; acetonitrile / 0 °C

With manganese(IV) oxide; triethylamine; magnesium bromide; In tetrahydrofuran; chloroform; acetonitrile;

DOI:10.1021/jm060021p

Reference yield:

6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazine-2-carboxylic acid ethyl ester (623564-59-0) → 6-[acetoxy-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]thiazin-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (1027013-15-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiBH₄ / methanol; tetrahydrofuran / 3 h / 20 - 40 °C

2.1: 1.78 g / MnO₂ / CHCl₃ / 1 h / Heating

3.1: MgBr₂; Et₃N / tetrahydrofuran; acetonitrile / -20 °C

3.2: tetrahydrofuran; acetonitrile / 0 °C

With manganese(IV) oxide; lithium borohydride; triethylamine; magnesium bromide; In tetrahydrofuran; methanol; chloroform; acetonitrile;

DOI:10.1021/jm060021p

upstream raw materials:

6,7-dihydro-4H-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]thiazin-2-yl)methanol

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