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

Base Information

• Chemical Name: (4S,5S)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
• CAS No.: 294195-95-2
• Molecular Formula: C₂₅H₂₄N₂O₄
• Molecular Weight: 416.477
• Mol file: 294195-95-2.mol

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

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

There total 5 articles about (4S,5S)-4,5-dihydroxy-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:

4,5-epoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (176970-20-0) → (4S,5S)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (294195-95-2) + (4R,5R)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

Guidance literature:

4,5-epoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine; With potassium hydroxide; In water; dimethyl sulfoxide; at 100 ℃; for 7h;

With vinyl acetate; Lipase QL; In di-isopropyl ether; N,N-dimethyl-formamide; at 40 ℃; for 22h;

With potassium carbonate; In methanol; at 20 ℃; for 0.5h;

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

Reference yield:

vinyl acetate (108-05-4,9003-20-7) + 4,5-epoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (176970-20-0) → (4S,5S)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (294195-95-2) + (4R,5R)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine + acetic acid 5-hydroxy-1-[4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester + acetic acid 5-hydroxy-1-[4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl ester

Guidance literature:

4,5-epoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine; With potassium hydroxide; In water; dimethyl sulfoxide; at 100 ℃; for 7h;

vinyl acetate; With Lipase QL; In di-isopropyl ether; N,N-dimethyl-formamide; at 40 ℃; Further byproducts given;

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)-4,5-dihydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (294195-95-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / thionyl chloride / CH₂Cl₂; dimethylformamide / 2 h / 20 °C

2: 38.0 g / sodium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 3.5 h / Heating

3: 75 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 h / 0 °C

4: 0.91 g

With thionyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Chlorination / 2: Dehydrochlorination / 3: Epoxidation;

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

upstream raw materials:

vinyl acetate

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

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:

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

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