4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6- bromo-7-oxo-, (4-nitrophenyl)methyl ester, (5R)-

Base Information

• Chemical Name: 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6- bromo-7-oxo-, (4-nitrophenyl)methyl ester, (5R)-
• CAS No.: 623565-64-0
• Molecular Formula: C22H19BrN4O8S
• Molecular Weight: 579.385
• Mol file: 623565-64-0.mol

Synonyms:

Chemical Property of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6- bromo-7-oxo-, (4-nitrophenyl)methyl ester, (5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6- bromo-7-oxo-, (4-nitrophenyl)methyl ester, (5R)-

There total 4 articles about 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6- bromo-7-oxo-, (4-nitrophenyl)methyl ester, (5R)- 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: 65.0%

6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-carbaldehyde (623565-63-9) + 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) → 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (623565-64-0)

Guidance literature:

6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-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 diethyl ether; triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile; at -20 ℃; for 2h;

acetic anhydride; In tetrahydrofuran; acetonitrile; at 0 ℃; for 15h;

DOI:10.1021/jm060021p

Reference yield: 65.0%

6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-carbaldehyde (623565-63-9) + acetic anhydride (108-24-7) → 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (623565-64-0)

Guidance literature:

6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-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 magnesium bromide ethyl etherate; triethylamine; In tetrahydrofuran; acetonitrile; at -20 ℃; for 2h;

acetic anhydride; In tetrahydrofuran; acetonitrile; at -20 - 0 ℃; for 15h;

Reference yield:

(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methanol (623565-62-8) → 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (623565-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / MnO₂ / CHCl₃ / 2 h / Heating

2.1: MgBr₂; Et₃N; Et₂O / tetrahydrofuran; acetonitrile / 2 h / -20 °C

2.2: 65 percent / tetrahydrofuran; acetonitrile / 15 h / 0 °C

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

DOI:10.1021/jm060021p

upstream raw materials:

6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazin-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-5H-pyrazolo[5,1-b][1,3]oxazin-2-yl)methanol