Phthaloyl-L-isoleucine

Base Information

• Chemical Name: Phthaloyl-L-isoleucine
• CAS No.: 29588-88-3
• Molecular Formula: C14H15NO4
• Molecular Weight: 261.277
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID601139573
• Nikkaji Number: J1.770.379J
• ChEMBL ID: CHEMBL2429922
• Mol file: 29588-88-3.mol

Synonyms:Phthaloyl-L-isoleucine;29588-88-3;PHT-ILE-OH;(2S,3S)-2-(1,3-Dioxoisoindolin-2-yl)-3-methylpentanoic acid;21844-63-3;(2S,3S)-2-(1,3-dioxoisoindol-2-yl)-3-methylpentanoic acid;N,N-Phthaloyl-L-isoleucine;CHEMBL2429922;SCHEMBL19359279;DTXSID601139573;MFCD00190998;AM81867;FD21849;AS-49225;Rel-(2s,3s)-2-(1,3-dioxoisoindolin-2-yl)-3-methylpentanoic acid;Rel-(2s,3s)-2-(1,3-dioxoisoindolin-2-yl)-3-methylpentanoicacid;(2S,3S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-methylpentanoic acid;(alphaS)-1,3-Dihydro-alpha-[(1S)-1-methylpropyl]-1,3-dioxo-2H-isoindole-2-acetic acid

Chemical Property of Phthaloyl-L-isoleucine

Chemical Property:

• Melting Point: 123-125℃
• PSA: 74.68000
• Density: 1.311
• LogP: 1.71980
• Storage Temp.: Store at 0°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 261.10010796
• Heavy Atom Count: 19
• Complexity: 382

Purity/Quality:

98%Min ^*data from raw suppliers

Phthaloyl-L-isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)N1C(=O)C2=CC=CC=C2C1=O
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)O)N1C(=O)C2=CC=CC=C2C1=O

Technology Process of Phthaloyl-L-isoleucine

There total 8 articles about Phthaloyl-L-isoleucine 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%

phthalic anhydride (85-44-9) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) → N-phthaloyl-L-isoleucine (29588-88-3)

Guidance literature:

at 135 ℃;

Reference yield: 99.0%

benzyl (2S,3S)-3-methyl-2-phthalimido-pentanoate (42406-41-7) → N-phthaloyl-L-isoleucine (29588-88-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4020(01)85232-7

Reference yield: 81.0%

L-isoleucine hydrochloride (17694-98-3) + methyl 2-(N-succinimidyloxycarbonyl)benzoate (438470-19-0) → N-phthaloyl-L-isoleucine (29588-88-3)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1021/jo016347h

upstream raw materials:

phthalic anhydride

DL-isoleucine

L-isoleucine

benzyl (2S,3S)-3-methyl-2-phthalimido-pentanoate

Refernces

• 1、 Vicens, Laia,Bietti, Massimo,Costas, Miquel. "General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C?H Bond Lactonization". supporting information. p. 4740 - 4746. Retrieved 2020/12/25.
• 2、 Dey, Aniruddha,Pimparkar, Sandeep,Deb, Arghya,Guin, Srimanta,Maiti, Debabrata. "Chelation-Assisted Palladium-Catalyzed γ-Arylation of Aliphatic Carboxylic Acid Derivatives". supporting information. p. 1301 - 1307. Retrieved 2017/04/18.