Enalapril diketopiperazine

Base Information

• Chemical Name: Enalapril diketopiperazine
• CAS No.: 115729-52-7
• Molecular Formula: C20H26N2O4
• Molecular Weight: 358.437
• Mol file: 115729-52-7.mol

Synonyms:2-[1,4-Dioxo-3-methyloctahydropyrrolo[1,2-a]pyrazine-2-yl]-4-phenylbutyric acid ethyl ester;4-Phenyl-2-[(1,2,3,4,6,7,8,8a-octahydro-3-methyl-1,4-dioxopyrrolo[1,2-a]pyrazin)-2-yl]butanoic acid ethyl ester;Enalapril diketopiperazine;(αS,3S,8aS)-Hexahydro-3-Methyl-1,4-dioxo-α-(2-phenylethyl)pyrrolo[1,2-a]pyrazine-2(1H)-acetic Acid Ethyl Ester;[3S-[2(R*),3α,8aβ]]-Hexahydro-3-Methyl-1,4-dioxo-α-(2-phenylethyl)pyrrolo[1,2-a]pyrazine-2(1H)-acetic Acid Ethyl Ester;Enalapril DKP;Enalapril IMpurity-D(EP);Enalapril EP IMpurity D

Chemical Property of Enalapril diketopiperazine

Chemical Property:

• Boiling Point: 562.9±50.0 °C(Predicted)
• PKA: -1.07±0.40(Predicted)
• PSA: 66.92000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 1.64840
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

EnalaprilDiketopiperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An impurity of Enalapril (E555250). Enalapril Diketopiperazine (Enalapril EP Impurity D) is an impurity of Enalapril (E555250).

Technology Process of Enalapril diketopiperazine

There total 2 articles about Enalapril diketopiperazine 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: 60.0%

enalapril (75847-73-3) → (S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester (115729-52-7)

Guidance literature:

In xylene; for 5h; Heating;

DOI:10.1016/S0022-2860(98)00399-8

Reference yield:

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride (84793-24-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) + enalaprilate (76420-72-9) + enalapril (75847-73-3) + (S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester (115729-52-7)

Guidance literature:

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride; L-proline; In water; ethyl acetate; at 19 - 20 ℃; for 5h; pH=10 - 11;

at 30 ℃; for 0.166667h; pH=4.3 - 4.7;

Reference yield:

(S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester (115729-52-7) → (R)-2-((3S,8aR)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid + (S)-2-((3S,8aR)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid

Guidance literature:

With tetramethyl ammoniumhydroxide; In ethanol; for 2h; Yield given. Yields of byproduct given;

DOI:10.1016/S0022-2860(98)00399-8

upstream raw materials:

enalapril

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride

L-proline

Refernces

• 1、 -. "Process for preparing pharmacologically acceptable salt of N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl amino acids". Example 1. . Retrieved 2008/06/13.