(4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 80366-56-9
• Molecular Formula: C₃₄H₃₆N₄O₇S₂
• Molecular Weight: 676.814

Synonyms:

Chemical Property of (4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

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Useful:

Technology Process of (4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 5 articles about (4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl 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: 52.0%

morpholinoethoxyamine hydrochloride (41155-82-2) + 4-(1,1-diphenylmethoxycarbonyl)-7-(2-thienylacetamido)-2α-methyl-3-formylceph-3-em 1-oxide (80366-51-4) → (4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (80366-56-9)

Guidance literature:

DOI:10.1248/cpb.31.1482

Reference yield:

diphenylmethyl 7-(2-thienylacetamido)-2-methylene-3-acetoxymethylceph-3-em-4-carboxylate (70056-19-8) → (4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (80366-56-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / Zn, formic acid / dimethylformamide / 20 h / Ambient temperature

2: 62 percent / 2 N HCl / dimethylformamide / 20 h / Ambient temperature

3: 36.2 percent / CrO₃, pyridine / CH₂Cl₂ / 0.08 h / 15 - 20 °C

4: 50 percent / MCPBA / CH₂Cl₂ / 1 h / Ambient temperature

5: 52 percent

With pyridine; chromium(VI) oxide; hydrogenchloride; formic acid; 3-chloro-benzenecarboperoxoic acid; zinc; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.31.1482

Reference yield:

diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-hydroxymethyl-ceph-2-em-4-carboxylate (80366-17-2) → (4R,6R,7R)-4-Methyl-3-[(2-morpholin-4-yl-ethoxyimino)-methyl]-5,8-dioxo-7-(2-thiophen-2-yl-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (80366-56-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 36.2 percent / CrO₃, pyridine / CH₂Cl₂ / 0.08 h / 15 - 20 °C

2: 50 percent / MCPBA / CH₂Cl₂ / 1 h / Ambient temperature

3: 52 percent

With pyridine; chromium(VI) oxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1248/cpb.31.1482

upstream raw materials:

morpholinoethoxyamine hydrochloride

4-(1,1-diphenylmethoxycarbonyl)-7-(2-thienylacetamido)-2α-methyl-3-formylceph-3-em 1-oxide

diphenylmethyl 7-(2-thienylacetamido)-2-methylene-3-acetoxymethylceph-3-em-4-carboxylate

diphenylmethyl 7-(2-thienylacetamido)-2-methyl-3-hydroxymethyl-ceph-2-em-4-carboxylate

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