N₂-[(3,5-difluoro-phenyl)acetyl]-N₁-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide

Base Information

• Chemical Name: N₂-[(3,5-difluoro-phenyl)acetyl]-N₁-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide
• CAS No.: 680229-09-8
• Molecular Formula: C₂₇H₂₄F₃N₃O₃
• Molecular Weight: 495.501

Synonyms:N₂-[(3,5-difluoro-phenyl)acetyl]-N₁-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide

Chemical Property of N₂-[(3,5-difluoro-phenyl)acetyl]-N₁-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide

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Technology Process of N₂-[(3,5-difluoro-phenyl)acetyl]-N₁-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide

There total 14 articles about N₂-[(3,5-difluoro-phenyl)acetyl]-N₁-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide 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:

3-amino-8-fluoro-4-phenyl-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one + N-(3,5-Difluorophenylacetyl)-L-alanine (208124-34-9) → N2-[(3,5-difluoro-phenyl)acetyl]-N1-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide (680229-09-8) + N2-[(3,5-difluoro-phenyl)acetyl]-N1-[(3R,4S)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; In dichloromethane; at 0 - 25 ℃; for 3h;

Reference yield:

(3,4-cis)-3-amino-8-fluoro-4-phenyl-1,3,4,5-tetrahydro-1H-benzazepin-2-one + N-(3,5-Difluorophenylacetyl)-L-alanine (208124-34-9) → N2-[(3,5-difluoro-phenyl)acetyl]-N1-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide (680229-09-8) + N2-[(3,5-difluoro-phenyl)acetyl]-N1-[(3R,4S)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 3h;

Reference yield:

(3,4-cis)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl methanesulfonate → N2-[(3,5-difluoro-phenyl)acetyl]-N1-[(3S,4R)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide (680229-09-8) + N2-[(3,5-difluoro-phenyl)acetyl]-N1-[(3R,4S)-8-fluoro-2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]-L-alaninamide

Guidance literature:

Multi-step reaction with 6 steps

1.1: 18-crown-6 ether / toluene / 12 h / 25 °C / Heating / reflux

2.1: lithium hydroxide / methanol; water / 5 h / 25 °C

2.2: pH 1 / Acidic conditions

3.1: pyridine / 27 h / 0 - 25 °C

4.1: sodium azide / N,N-dimethyl-formamide / 24 h / 25 - 90 °C

5.1: PS-triphenylphosphine / tetrahydrofuran / 24 h / 25 °C

6.1: 4-methyl-morpholine; benzotriazol-1-ol / dichloromethane / 3 h / 0 - 25 °C

With 4-methyl-morpholine; lithium hydroxide; sodium azide; PS-triphenylphosphine; benzotriazol-1-ol; 18-crown-6 ether; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

N-(3,5-Difluorophenylacetyl)-L-alanine

(S)-2-[(3,5-difluorophenyl)acetamido]propanoic acid methyl ester

dimethyl [2-(2-amino-4-fluorophenyl)-1-phenylethyl]malonate

dimethyl [2-(4-fluoro-2-nitrophenyl)-1-phenylethyl]malonate

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