(4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Base Information

• Chemical Name: (4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
• CAS No.: 294196-32-0
• Molecular Formula: C₂₆H₂₆N₂O₄
• Molecular Weight: 430.503
• Mol file: 294196-32-0.mol

Synonyms:(4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property of (4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

There total 5 articles about (4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 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: 83.0%

(4S,5S)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (294195-95-2) + methyl iodide (74-88-4) → (4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (294196-32-0)

Guidance literature:

(4S,5S)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine; With di(n-butyl)tin oxide; In 1,4-dioxane; toluene; for 22h; Heating;

methyl iodide; With tetrabutylammomium bromide; In 1,4-dioxane; toluene; at 100 - 110 ℃; for 9.5h;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

5-hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (150681-19-9) → (4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (294196-32-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / thionyl chloride / CH₂Cl₂; dimethylformamide / 2 h / 20 °C

2.1: 38.0 g / sodium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 3.5 h / Heating

3.1: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 h / 0 °C

4.1: 0.91 g

5.1: dibutyltin oxide / toluene; dioxane / 22 h / Heating

5.2: 83 percent / tetrabutylammonium bromide / toluene; dioxane / 9.5 h / 100 - 110 °C

With thionyl chloride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Chlorination / 2.1: Dehydrochlorination / 3.1: Epoxidation / 5.1: Cyclization / 5.2: Ring cleavage;

DOI:10.1016/S0040-4020(00)00388-4

Reference yield:

1-[4-(2-methylbenzoylamino)benzoyl]-2,3-dihydro-1H-1-benzazepine (176970-19-7) → (4S,5S)-4-hydroxy-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (294196-32-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 h / 0 °C

2.1: 0.91 g

3.1: dibutyltin oxide / toluene; dioxane / 22 h / Heating

3.2: 83 percent / tetrabutylammonium bromide / toluene; dioxane / 9.5 h / 100 - 110 °C

With di(n-butyl)tin oxide; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; dichloromethane; toluene; 1.1: Epoxidation / 3.1: Cyclization / 3.2: Ring cleavage;

DOI:10.1016/S0040-4020(00)00388-4

upstream raw materials:

(4S,5S)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

methyl iodide

5-hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

1-[4-(2-methylbenzoylamino)benzoyl]-2,3-dihydro-1H-1-benzazepine

Downstream raw materials:

O-methyl O-(4S,5S)-5-methoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-4-yl thiocarbonate