1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, monohydrochloride, [S-(R*,S*)]-

Base Information

• Chemical Name: 1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, monohydrochloride, [S-(R*,S*)]-
• CAS No.: 86541-77-7
• Molecular Formula: C24H28N2O5^.HCl
• Molecular Weight: 460.958
• Hs Code.: 2933790002
• Mol file: 86541-77-7.mol

Synonyms:Benazepril hydrochloride;1H-1-Benzazepine-1-acetic acid,3-[[(1R)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-,monohydrochloride,(3S);2-((S)-3-((R)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)aceticacidhydrochloride;(3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride;2,6-BIS(HYDROXYMETHYL)-4-METHOXYPHENOL;(1'S,3S)-3-<(1'-(ethoxycarbonyl)-3'-phenylpropyl)amino>-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-essigsaeure-hydrochlorid;

Chemical Property of 1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, monohydrochloride, [S-(R*,S*)]-

Chemical Property:

• Melting Point: 181-183 °C(Solv: 2-butanone (78-93-3))
• PSA: 95.94000
• LogP: 3.83100

Purity/Quality:

90-99.99% ^*data from raw suppliers

(1R,3S)-BenazeprilHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1R,3S)-Benazepril Hydrochloride is an isomer of Benazepril (B119750), an angiotensin converting enzyme inhibitor and a antihypertensive agent.

Technology Process of 1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, monohydrochloride, [S-(R*,S*)]-

There total 18 articles about 1H-1-Benzazepine-1-acetic acid, 3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-, monohydrochloride, [S-(R*,S*)]- 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: 84.0%

(R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester (109010-59-5) + tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (109010-60-8) → (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride (86541-77-7,215447-89-5,88372-38-7)

Guidance literature:

With 4-methyl-morpholine; hydrogenchloride; at 80 ℃; for 9h;

DOI:10.1002/hlca.19880710205

Reference yield: 25.0%

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) + (3S)-3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one sodium salt (86499-53-8) → benazepril hydrochloride (86541-74-4,215447-89-5,88372-38-7) + (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride (86541-77-7,215447-89-5,88372-38-7)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid; Ambient temperature;

DOI:10.1021/jm00148a023

Reference yield:

ethyl (R)-2-hydroxy-4-phenylbutyrate (90315-82-5) → (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride (86541-77-7,215447-89-5,88372-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / Et₃N / toluene / 1 h / Ambient temperature

2: 84 percent / N-methylmorpholin, HCl / 9 h / 80 °C

With 4-methyl-morpholine; hydrogenchloride; triethylamine; In toluene;

DOI:10.1002/hlca.19880710205

upstream raw materials:

2-oxo-4-phenylbutanoic acid ethyl ester

(3S)-3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one sodium salt

(R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester

tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate

Downstream raw materials:

(3S)-1-(carboxymethyl)-<<(1S)-1-carboxy-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one

Refernces

• 1、 Boyer,Pfund r.,Portmann,Sedelmeier,Wetter. "Note on the synthesis of an optically active ACE inhibitor with amino-oxo-benzazepine-1-alkanoic-acid structure by means of an enantioconvergent crystallization-based resolution". . p. 337 - 343. Retrieved 2007/10/02.