Cyclo(aspartyl-phenylalanyl)

Base Information

• Chemical Name: Cyclo(aspartyl-phenylalanyl)
• CAS No.: 5262-10-2
• Molecular Formula: C13H14 N2 O4
• Molecular Weight: 262.265
• Hs Code.: 2933599090
• European Community (EC) Number: 226-075-1
• UNII: ZM82VP15YJ
• DSSTox Substance ID: DTXSID60200600
• Nikkaji Number: J297.963B
• Wikidata: Q27295736
• ChEMBL ID: CHEMBL1213197
• Mol file: 5262-10-2.mol

Synonyms:cyclo(Asp-Phe);cyclo(aspartyl-phenylalanyl)

Chemical Property of Cyclo(aspartyl-phenylalanyl)

Chemical Property:

• Vapor Pressure: 1.02E-18mmHg at 25°C
• Melting Point: 270-272 °C(lit.)
• Boiling Point: 667.4°Cat760mmHg
• PKA: 4.02±0.10(Predicted)
• Flash Point: 357.4°C
• PSA: 95.50000
• Density: 1.298g/cm³
• LogP: 0.34460
• Storage Temp.: -15°C
• Solubility.: Acetic Acid (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Very Sligh
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 262.09535693
• Heavy Atom Count: 19
• Complexity: 377

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,5S)-5-Benzyl-3,6-dioxo-2-piperazineaceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC2C(=O)NC(C(=O)N2)CC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)C[C@H]2C(=O)N[C@H](C(=O)N2)CC(=O)O
• Uses: The diketopiperazine impurity of the sweetening agent Aspartame (A790015). It is also found in in processed cocoa powder. (2S,5S)-5-Benzyl-3,6-dioxo-2-piperazineacetic Acid (Aspartame EP Impurity A) is the diketopiperazine impurity of the sweetening agent Aspartame (A790015). It is also found in in processed cocoa powder.

Technology Process of Cyclo(aspartyl-phenylalanyl)

There total 4 articles about Cyclo(aspartyl-phenylalanyl) 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: 92.0%

L-Asp-L-Phe-OMe (22839-47-0,7421-84-3) → [(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid (5262-10-2)

Guidance literature:

at 200 ℃; for 0.333333h;

DOI:10.1007/BF00814141

Reference yield:

L-Asp-L-Phe-OMe (22839-47-0,7421-84-3) → methanol (67-56-1) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + [(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid (5262-10-2)

Guidance literature:

With water; In methanol; at 60 ℃; Rate constant; Kinetics; Thermodynamic data; E(a), var. water:alcohol solutions;

DOI:10.1002/jps.2600800713

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → [(2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl]acetic acid (5262-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; ethyl acetate / Ambient temperature

2: 92 percent / 0.33 h / 200 °C

In diethyl ether; ethyl acetate;

DOI:10.1007/BF00814141

upstream raw materials:

L-Asp-L-Phe-OMe

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

Downstream raw materials:

(S)-2-(2-((2S,5S)-5-benzyl-3,6-dioxopiperazin-2-yl)acetamido)-6-ethanethioamido-N-(2-oxo-2-phenylethyl)hexanamide

((2S,5S)-5-Benzyl-3,6-dioxo-piperazin-2-yl)-acetic acid 11-bromo-undecyl ester

cyclo(L-10-bromodecylasparaginyl-L-phenylalanine)

Refernces

• 1、 Rastogi,Zakrzewski,Suryanarayanan. "Investigation of solid-state reactions using variable temperature X-ray powder diffractrometry. I. Aspartame hemihydrate". . p. 267 - 273. Retrieved 2007/10/03.
• 2、 Burger, K.,Rudolph, M.,Windeisen, E.,Worku, A.,Fehn, S.. "Hexafluoroacetone as Protecting Group and Activating Reagent in Amino Acid and Peptide Chemistry, XI. A New Simple Preparative Access to 2,5-Dioxopiperazines and 2,5-Dioxomorpholines". . p. 453 - 464. Retrieved 2007/10/02.