p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate
• CAS No.: 89051-52-5
• Molecular Formula: C₁₅H₁₅ClN₂O₅S
• Molecular Weight: 370.813
• Mol file: 89051-52-5.mol

Synonyms:p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate

Chemical Property of p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate

There total 7 articles about p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-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: 91.0%

p-nitrobenzyl <(R)-4-(2-benzothiazol-2-yldithio)-2-oxo-1-azetidinyl>isopropenylacetate (71355-12-9,95835-16-8) → di(benzothiazol-2-yl)disulfide (120-78-5) + p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate (89051-52-5)

Guidance literature:

With hydrogenchloride; sodium nitrite; In dichloromethane; at 0 ℃; for 2h; Product distribution; Mechanism; reactions of derivatives with HCl and HBr;

DOI:10.1246/bcsj.62.3046

Reference yield: 90.0%

p-nitrobenzyl <(R)-4-(2-benzothiazol-2-yldithio)-2-oxo-1-azetidinyl>isopropenylacetate (71355-12-9,95835-16-8) → p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate (89051-52-5)

Guidance literature:

With copper dichloride; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1055/s-1986-31587

Reference yield:

2,2-dimethylpenam-3α-carboxylic acid 1-oxide p-nitrobenzyl ester (71355-11-8,72554-59-7,78739-16-9) → p-nitrobenzyl 2β-(chloromethyl)-2α-methylpenam-3α-carboxylate (89051-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 2.5 h / Heating

2: cupric chloride / CH₂Cl₂ / 4 h / Ambient temperature

With copper dichloride; In dichloromethane; toluene;

upstream raw materials:

p-nitrobenzyl <(R)-4-(2-benzothiazol-2-yldithio)-2-oxo-1-azetidinyl>isopropenylacetate

2,2-dimethylpenam-3α-carboxylic acid 1-oxide p-nitrobenzyl ester

(R)-3-Methyl-2-[2-(5-{1-[(R)-2-methyl-1-(4-nitro-benzyloxycarbonyl)-allyl]-4-oxo-azetidin-2-yldisulfanyl}-[1,3,4]thiadiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-but-3-enoic acid 4-nitro-benzyl ester