3-((2S,5S)-5-Methyl-3,6-dioxopiperazin-2-yl)propanoic acid

Base Information

• Chemical Name: 3-((2S,5S)-5-Methyl-3,6-dioxopiperazin-2-yl)propanoic acid
• CAS No.: 16364-36-6
• Molecular Formula: C₈H₁₂N₂O₄
• Molecular Weight: 200.194
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID40429392
• Wikidata: Q82242413
• Mol file: 16364-36-6.mol

Synonyms:Cyclo(-Ala-Glu);16364-36-6;3-((2S,5S)-5-Methyl-3,6-dioxopiperazin-2-yl)propanoic acid;Cyclo(Ala-Glu);3-[(2S,5S)-5-methyl-3,6-dioxopiperazin-2-yl]propanoic acid;cyclo-L-Ala-L-Glu(OH);CYCLO(L-ALAL-L-GLU);DTXSID40429392;GWFWPFQFBPEFQN-WHFBIAKZSA-N;MFCD05663454;AKOS022181519;AT17625;HY-131110;CS-0128554

Chemical Property of 3-((2S,5S)-5-Methyl-3,6-dioxopiperazin-2-yl)propanoic acid

Chemical Property:

• Boiling Point: 621.2±40.0 °C(Predicted)
• PKA: 4.47±0.10(Predicted)
• PSA: 95.50000
• Density: 1.249±0.06 g/cm3(Predicted)
• LogP: -0.48810
• Storage Temp.: -15°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 200.07970687
• Heavy Atom Count: 14
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

CYCLO(-ALA-GLU) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)N1)CCC(=O)O
• Isomeric SMILES: C[C@H]1C(=O)N[C@H](C(=O)N1)CCC(=O)O
• Uses: CYCLO(-ALA-GLU) is used in the preparation of cyclic dipeptides ?containing anti-?obesity composition.

Technology Process of 3-((2S,5S)-5-Methyl-3,6-dioxopiperazin-2-yl)propanoic acid

There total 5 articles about 3-((2S,5S)-5-Methyl-3,6-dioxopiperazin-2-yl)propanoic acid 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: 94.0%

Cyclo-[Ala-Glu(OBzl)] (87378-38-9) → Cyclo-[Ala-Glu] (16364-36-6)

Guidance literature:

With hydrogen; palladium; In 2,2,2-trifluoroethanol; for 48h;

Reference yield:

C21H23N3O7 → Cyclo-[Ala-Glu] (16364-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methyl-morpholine / ethyl acetate / 12 h / pH 9 - 9.5

2: palladium; hydrogen / 2,2,2-trifluoroethanol / 48 h

With 4-methyl-morpholine; hydrogen; palladium; In 2,2,2-trifluoroethanol; ethyl acetate;

DOI:10.1002/cmdc.201600157

Reference yield:

L-glutamic acid γ-benzyl ester (1676-73-9,25014-27-1) → Cyclo-[Ala-Glu] (16364-36-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 4-methyl-morpholine / 1,4-dioxane; water / 12 h / 20 °C

2.1: ethyl acetate / 1 h / 0 °C

2.2: 5 h / 0 - 20 °C

3.1: trifluoroacetic acid / tetrahydrofuran / 1 h / -15 - 20 °C

4.1: 4-methyl-morpholine / ethyl acetate / 12 h / pH 9 - 9.5

5.1: palladium; hydrogen / 2,2,2-trifluoroethanol / 48 h

With 4-methyl-morpholine; hydrogen; palladium; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; 2,2,2-trifluoroethanol; water; ethyl acetate;

DOI:10.1002/cmdc.201600157

upstream raw materials:

Cyclo-[Ala-Glu(OBzl)]

L-glutamic acid γ-benzyl ester

Boc-Ala-Glu(OBzl)-OH

Boc-Ala-Glu(OBzl)-ONp