LY 289790

Base Information

• Chemical Name: LY 289790
• CAS No.: 36923-27-0
• Molecular Formula: C15H14N2O5S
• Molecular Weight: 334.34700
• Mol file: 36923-27-0.mol

Synonyms:(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid;

Chemical Property of LY 289790

Chemical Property:

• PSA: 121.24000
• LogP: 0.76260

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of LY 289790

There total 13 articles about LY 289790 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: 58.0%

p-nitrobenzyl (2R,3R)-7-phenoxyacetylaminoceph-3-em-4-carboxylate (64836-37-9) → (6R,7R)-7-(phenoxyacetamido)ceph-3-em-4-carboxylic acid (36923-27-0)

Guidance literature:

With phosphate buffer; hydrogen; palladium on activated charcoal; In ethyl acetate; for 1.5h; Ambient temperature;

Reference yield:

(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dimethyl ester (380412-97-5) → (6R,7R)-7-(phenoxyacetamido)ceph-3-em-4-carboxylic acid (36923-27-0) + (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid (177703-38-7)

Guidance literature:

With potassium hydroxide; In pyridine; at -8 ℃; for 2.5h; Title compound not separated from byproducts;

DOI:10.1139/v01-100

Reference yield:

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one (35500-75-5) → (6R,7R)-7-(phenoxyacetamido)ceph-3-em-4-carboxylic acid (36923-27-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 50 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

2.1: 94 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / 2 h / 0 °C

3.1: ozone / CH₂Cl₂; methanol / -78 °C

3.2: 100 percent / dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

4.1: 8.0 g / aqueous perchloric acid / CH₂Cl₂; acetone / 1.5 h

5.1: sulfuric acid / acetic acid / 2.5 h

6.1: 489 mg / p-toluenesulfonic acid monohydrate / toluene / Heating

7.1: aqueous potassium hydroxide / pyridine / 2.5 h / -8 °C

With potassium hydroxide; perchloric acid; sulfuric acid; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; ozone; In pyridine; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1139/v01-100

upstream raw materials:

p-nitrobenzyl (2R,3R)-7-phenoxyacetylaminoceph-3-em-4-carboxylate

(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dimethyl ester

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one

3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid methyl ester