1-[3-(Acetylsulfanyl)-2-methylpropanoyl]prolylphenylalanine

Base Information

• Chemical Name: 1-[3-(Acetylsulfanyl)-2-methylpropanoyl]prolylphenylalanine
• CAS No.: 74258-86-9
• Molecular Formula: C20H26N2O5S
• Molecular Weight: 406.503
• NSC Number: 338157
• DSSTox Substance ID: DTXSID10860970
• ChEMBL ID: CHEMBL91800
• Mol file: 74258-86-9.mol

Synonyms:1-[3-(acetylsulfanyl)-2-methylpropanoyl]prolylphenylalanine;CHEMBL91800;DTXSID10860970;NSC338157;AKOS040759265;FT-0630834

Chemical Property of 1-[3-(Acetylsulfanyl)-2-methylpropanoyl]prolylphenylalanine

Chemical Property:

• Vapor Pressure: 2.26E-19mmHg at 25°C
• Melting Point: 155-156°
• Refractive Index: 1.581
• Boiling Point: 679.1 °C at 760 mmHg
• Flash Point: 364.5 °C
• PSA: 129.08000
• Density: 1.281 g/cm³
• LogP: 2.03410
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 406.15624311
• Heavy Atom Count: 28
• Complexity: 591

Purity/Quality:

99% ^*data from raw suppliers

Alacepril ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CSC(=O)C)C(=O)N1CCCC1C(=O)NC(CC2=CC=CC=C2)C(=O)O
• Description: Alacepril is an angiotensin-converting enzyme (ACE) inhibitor useful in the treatment of essential and renal hypertension. Compared with captopril, alacepril is a weaker ACE inhibitor in vino, yet clinically it has a longer duration of action and appears to be more active due to an added component of norepinephrine antagonism.
• Therapeutic Function: Antihypertensive

Technology Process of 1-[3-(Acetylsulfanyl)-2-methylpropanoyl]prolylphenylalanine

There total 8 articles about 1-[3-(Acetylsulfanyl)-2-methylpropanoyl]prolylphenylalanine 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: 100.0%

1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-L-phenylalanine tert-butyl ester (74258-85-8) → alacepril (74258-86-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

Reference yield: 65.0%

(2R,S)-3-Acetylthio-2-methylpropanoyl chloride (74345-73-6) + L-prolyl-L-phenylalanine (13589-02-1) → alacepril (74258-86-9)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; for 2h; Ambient temperature;

DOI:10.1248/cpb.38.529

Reference yield:

1-(D-3-Acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester → alacepril (74258-86-9)

Guidance literature:

In methoxybenzene; trifluoroacetic acid;

upstream raw materials:

(2R,S)-3-Acetylthio-2-methylpropanoyl chloride

L-prolyl-L-phenylalanine

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(S)-methyl 2-((S)-1-formylpyrrolidine-2-carbonylamino)-3-phenylpropanoate

Downstream raw materials:

1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-L-phenylalanine 3-bromomethyl phenyl ester

1-((S)-3-mercapto-2-methylpropanoyl)-L-prolyl-L-phenylalanine

Refernces

• 1、 Sawayama,Itokawa,Shimada,Doi,Kimura,Nishim ura. "Synthesis of 1-((S)-3-acetylthio-2-methylpropanoyl)-L-pro pyl-L-phenylalanine (alacepril) and one of its active metabolites, the desacetyl derivative (DU-1227)". . p. 529 - 531. Retrieved 2007/10/02.