(5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-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: (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 852671-32-0
• Molecular Formula: C₄₁H₃₁N₃O₈S₂
• Molecular Weight: 757.844

Synonyms:(5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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Technology Process of (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 7 articles about (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-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:

(7-oxo-7H-phenoxazin-3-yloxy)-acetaldehyde (609812-80-8) + [(6R,7R)-2-Benzhydryloxycarbonyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-triphenyl-phosphonium; iodide → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (852671-32-0)

Guidance literature:

[(6R,7R)-2-Benzhydryloxycarbonyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-triphenyl-phosphonium; iodide; With sodium hydroxide; In dichloromethane; at 20 ℃; for 0.5h;

(7-oxo-7H-phenoxazin-3-yloxy)-acetaldehyde; In dichloromethane; at 20 ℃;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1021/ja036126o

Reference yield:

2-thienylacetic acid chloride (39098-97-0) → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (852671-32-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / Et₃N; 2,6-lutidine / acetonitrile / 4 h / 0 - 20 °C

2.1: NaI / acetone / 1 h / 20 °C

3.1: 0.877 g / ethyl acetate

4.1: aq. NaOH / CH₂Cl₂ / 0.5 h / 20 °C

4.2: CH₂Cl₂ / 20 °C

4.3: m-CPBA / CH₂Cl₂ / 0.67 h / 0 °C

With 2,6-dimethylpyridine; sodium hydroxide; triethylamine; sodium iodide; In dichloromethane; ethyl acetate; acetone; acetonitrile; 4.2: Wittig reaction;

DOI:10.1021/ja036126o

Reference yield:

7-hydroxy-3H-phenoxazin-3-one sodium salt (34994-50-8) → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(7-oxo-7H-phenoxazin-3-yloxy)-propenyl]-7-(2-thiophen-2-yl-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (852671-32-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 35 percent / K₂CO₃ / dimethylformamide / 48 h / 115 - 120 °C

2.1: aq. HCl / CHCl₃ / 0.2 h

3.1: aq. NaOH / CH₂Cl₂ / 0.5 h / 20 °C

3.2: CH₂Cl₂ / 20 °C

3.3: m-CPBA / CH₂Cl₂ / 0.67 h / 0 °C

With hydrogenchloride; sodium hydroxide; potassium carbonate; In dichloromethane; chloroform; N,N-dimethyl-formamide; 3.2: Wittig reaction;

DOI:10.1021/ja036126o

upstream raw materials:

(7-oxo-7H-phenoxazin-3-yloxy)-acetaldehyde

2-thienylacetic acid chloride

7-hydroxy-3H-phenoxazin-3-one sodium salt

(6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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