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

Base Information

• Chemical Name: 10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester
• CAS No.: 70850-45-2
• Molecular Formula: C₂₃H₂₃N₃O₉S
• Molecular Weight: 517.516

Synonyms:10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

Chemical Property of 10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

Chemical Property:

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Technology Process of 10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

There total 1 articles about 10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl 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:

10-chloroacetoxy-1α-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid 4-nitro-benzyl ester (70878-66-9) → 10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid 4-nitro-benzyl ester (70850-45-2)

Guidance literature:

With thiourea; In ethanol;

DOI:10.1021/jo01331a028

Reference yield: 85.0%

10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid 4-nitro-benzyl ester (70850-45-2) → (2S,3R,4S,5R,6R)-3-Formyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (111924-23-3)

Guidance literature:

With dimethyl sulfoxide; In acetic anhydride; at 20 ℃;

DOI:10.1039/c39870000081

Reference yield:

10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid 4-nitro-benzyl ester (70850-45-2) → (5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (64370-34-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / dimethyl sulphoxide / acetic anhydride / 20 °C

2: 90 percent / sodium chlorite, resorcinol / tetrahydrofuran; H₂O; various solvent(s) / pH 3.5

3: oxalyl chloride, pyridine / CH₂Cl₂ / 1.) 0 deg C, 2.) 16 h, room temperature

With pyridine; sodium chlorite; oxalyl dichloride; dimethyl sulfoxide; recorcinol; In tetrahydrofuran; dichloromethane; water; acetic anhydride;

DOI:10.1039/c39870000081

upstream raw materials:

10-chloroacetoxy-1α-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

Downstream raw materials:

(2S,3R,4S,5R,6R)-3-Formyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

(5R)-3-methyl-7-oxo-6t-(2-phenoxy-acetylamino)-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

4-nitrobenzyl (3R,5R,6R)-2-methylene-6-(phenoxyacetamido)penam-3-carboxylate

(2S,3R,5R,6R)-3-Methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

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