4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: 4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 58244-55-6
• Molecular Formula: C₂₃H₂₃N₃O₇S
• Molecular Weight: 485.518

Synonyms:4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property of 4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

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Technology Process of 4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate

There total 2 articles about 4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-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: 97.0%

penicillin V potassium (132-98-9) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate (58244-55-6)

Guidance literature:

With sodium iodide; In N,N-dimethyl-formamide; for 15h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91148-2

Reference yield:

6-aminopenicillanic acid p-nitrobenzyl ester (29750-72-9) + Phenoxyacetyl chloride (701-99-5) → 4-nitrobenzyl(2S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate (58244-55-6)

Guidance literature:

With triethylamine; In dichloromethane; for 3h; Yield given; Ambient temperature;

DOI:10.1055/s-1983-30419

Reference yield: 96.0%

(S)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (58244-55-6,67807-63-0,87018-70-0) → (S)-3,3-Dimethyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (29707-62-8,41625-65-4,68000-26-0,70145-05-0,84278-68-2)

Guidance literature:

With formic acid; dihydrogen peroxide; In dichloromethane; at 0 - 5 ℃; for 3h;

DOI:10.1055/s-1989-27194

upstream raw materials:

6-aminopenicillanic acid p-nitrobenzyl ester

Phenoxyacetyl chloride

penicillin V potassium

1-bromomethyl-4-nitro-benzene

Downstream raw materials:

1β-cyanoimino-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

(2S,5R,6R)-6-[tert-Butoxycarbonyl-(2-phenoxy-acetyl)-amino]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

4-nitrobenzyl(2S,4S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate 4-oxide

2-[(2R,3R)-2-Acetylsulfanyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid 4-nitro-benzyl ester

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