Enalapril Diketopiperazine

Base Information

• Chemical Name: Enalapril Diketopiperazine
• CAS No.: 115729-52-7
• Molecular Formula: C20H26N2O4
• Molecular Weight: 358.437
• European Community (EC) Number: 641-574-8
• UNII: 609HCJ5DV4
• DSSTox Substance ID: DTXSID10151178
• Wikidata: Q27263200
• Mol file: 115729-52-7.mol

Synonyms:Enalapril Diketopiperazine;115729-52-7;Enalapril DKP;Enalapril impurity D;609HCJ5DV4;Ethyl (2S)-2-((3S,8aS)-3-methyl-1,4-dioxo-octahydropyrrolo(1,2-a)pyrazin-2-yl)-4-phenylbutanoate;ethyl (2S)-2-[(3S,8aS)-3-methyl-1,4-dioxo-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazin-2-yl]-4-phenylbutanoate;UNII-609HCJ5DV4;Enalapril maleate impurity D [EP];Ethyl (2S)-2-[(3S,8aS)-3-Methyl-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-2-yl]-4-phenylbutanoate (Enalapril Diketopiperazine);Enalapril maleate specified impurity D [EP];DTXSID10151178;Pyrrolo(1,2-a)pyrazine-2(1H)-acetic acid, hexahydro-3-methyl-1,4-dioxo-alpha-(2-phenylethyl)-, ethyl ester, (3S-(2(R*),3alpha,8abeta))-;Pyrrolo(1,2-a)pyrazine-2(1H)-acetic acid, hexahydro-3-methyl-1,4-dioxo-alpha-(2-phenylethyl)-, ethyl ester, (alphaS,3S,8aS)-;ENALAPRIL MALEATE IMPURITY D [EP IMPURITY];Q27263200;PYRROLO(1,2-A)PYRAZINE-2(1H)-ACETIC ACID, HEXAHYDRO-3-METHYL-1,4-DIOXO-.ALPHA.-(2-PHENYLETHYL)-, ETHYL ESTER, (.ALPHA.S,3S,8AS)-;PYRROLO(1,2-A)PYRAZINE-2(1H)-ACETIC ACID, HEXAHYDRO-3-METHYL-1,4-DIOXO-.ALPHA.-(2-PHENYLETHYL)-, ETHYL ESTER, (3S-(2(R*),3.ALPHA.,8A.BETA.))-

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)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 358.18925731
• Heavy Atom Count: 26
• Complexity: 544

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:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)N2C(C(=O)N3CCCC3C2=O)C
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N2[C@H](C(=O)N3CCC[C@H]3C2=O)C
• 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