(5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-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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Chemical Name:(5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-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.:623564-21-6
Molecular Formula:C₂₃H₂₂BrN₅O₇S
Molecular Weight:592.427
Hs Code.:

(5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Synonyms:(5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-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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Chemical Property of (5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-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-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-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 5 articles about (5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-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: 21.0%

: 623564-20-5
7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbaldehyde

: 108-24-7
acetic anhydride

: 623564-16-9
(5R,6S)-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

: 623564-21-6
(5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Guidance literature:: 7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-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 8h;

acetic anhydride; In tetrahydrofuran; acetonitrile; at 0 ℃; for 15h;
DOI:10.1021/jm060021p

Reference yield:

: 108-24-7
acetic anhydride

: 623564-21-6
(5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Guidance literature:: 7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbaldehyde; With triethylamine; magnesium bromide; In tetrahydrofuran; acetonitrile; at -20 ℃; for 4.5h;

acetic anhydride; In tetrahydrofuran; acetonitrile; at -20 - 0 ℃; for 17h;

Reference yield:

: 77112-52-8
ethyl imidazo[1,2-a]pyrazine-2-carboxylate

: 623564-21-6
(5R,6RS)-6-[(RS)-acetoxy-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitrobenzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 63 percent / H₂; HCl / Pd/C / ethanol / 15 h / 20 °C / 2068.59 Torr

2.1: 57 percent / Et₃N; NaBH₃CN / methanol / 3.5 h / 20 °C

3.1: 42 percent / DIBAL / toluene; CH₂Cl₂ / 2 h / -78 °C

4.1: MgBr₂; Et₃N; Et₂O / tetrahydrofuran; acetonitrile / 8 h / -20 °C

4.2: 21 percent / tetrahydrofuran; acetonitrile / 15 h / 0 °C

With hydrogenchloride; diethyl ether; hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; magnesium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jm060021p