4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate
• CAS No.: 153836-85-2
• Molecular Formula: C₃₄H₃₈N₆O₁₁S
• Molecular Weight: 738.775

Synonyms:

Chemical Property of 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate

There total 4 articles about 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-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:

(2S,4S)-4-(4-methoxy-benzylthio)-1-methyl-2-pyrrolidinecarboxylic acid (127423-28-3) → 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (153836-85-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N'-carbonyldiimidazole / acetonitrile / 1 h / 40 °C

1.2: 1.21 g / diisopropylethylamine / acetonitrile; methanol / 1.5 h / 20 °C

2.1: 0.85 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h

3.1: 0.42 g / anisole; trifluoromethanesulfonic acid / trifluoroacetic acid / 1.5 h / 20 °C

4.1: 0.25 g / diisopropylethylamine / acetonitrile / 48 h

With trifluorormethanesulfonic acid; methoxybenzene; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In dichloromethane; acetonitrile; trifluoroacetic acid;

DOI:10.7164/antibiotics.54.1080

Reference yield:

(2S,4S)-2-(3-aminoazetidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-methylpyrrolidine (153836-32-9) → 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (153836-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.85 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h

2: 0.42 g / anisole; trifluoromethanesulfonic acid / trifluoroacetic acid / 1.5 h / 20 °C

3: 0.25 g / diisopropylethylamine / acetonitrile / 48 h

With trifluorormethanesulfonic acid; methoxybenzene; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; trifluoroacetic acid;

DOI:10.7164/antibiotics.54.1080

Reference yield:

(2S,4S)-4-(4-methoxybenzylthio)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidine (153836-33-0) → 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (153836-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.42 g / anisole; trifluoromethanesulfonic acid / trifluoroacetic acid / 1.5 h / 20 °C

2: 0.25 g / diisopropylethylamine / acetonitrile / 48 h

With trifluorormethanesulfonic acid; methoxybenzene; N-ethyl-N,N-diisopropylamine; In acetonitrile; trifluoroacetic acid;

DOI:10.7164/antibiotics.54.1080

upstream raw materials:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(2S,4S)-4-mercapto-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-yl-carbonyl]pyrrolidine

(2S,4S)-4-(4-methoxy-benzylthio)-1-methyl-2-pyrrolidinecarboxylic acid

(2S,4S)-2-(3-aminoazetidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-methylpyrrolidine

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