N-Phthaloyl-L-phenylalanine

Base Information

• Chemical Name: N-Phthaloyl-L-phenylalanine
• CAS No.: 5123-55-7
• Molecular Formula: C17H13 N O4
• Molecular Weight: 295.295
• Hs Code.: 2925190090
• European Community (EC) Number: 610-635-0
• NSC Number: 338600
• DSSTox Substance ID: DTXSID70319030
• Nikkaji Number: J784.214G
• Wikidata: Q72499384
• ChEMBL ID: CHEMBL1331094
• Mol file: 5123-55-7.mol

Synonyms:N-Phthaloyl-L-phenylalanine;5123-55-7;N-Pht-Phe-OH;Phthaloyl-L-phenylalanine;N-Phthalyl-L-phenylalanine;(S)-N-Phthaloylphenylalanine;(2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoic acid;(2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-3-phenylpropanoic acid;2-Isoindolineacetic acid, .alpha.-benzyl-1,3-dioxo-, (S)-(-)-;2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-.alpha.-(phenylmethyl)-, (S)-;N-Phthaloyl-Phe-OH;NSC-19760;NCIStruc1_000419;NCIStruc2_000615;SCHEMBL392680;N,N-Phthaloyl-L-phenylalanine;CHEMBL1331094;DTXSID70319030;NCI19760;CCG-38000;MFCD00069738;NCGC00013262;NSC338600;AKOS015903142;AM82174;CS-W009977;NSC 338600;NSC-338600;3-phenyl-2(S)-phthalimidopropionic acid;NCGC00013262-02;NCGC00096381-01;AS-46920;P1227;EN300-95018;F10912;2-Isoindolineacetic acid,3-dioxo-, (S)-(-)-;N-Phthaloyl-L-phenylalanine, >=99.0% (TLC);(s)-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoic acid;2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanoic acid #;2H-Isoindole-2-acetic acid, 1,3-dihydro-1,3-dioxo-a-(phenylmethyl)-,(aS)-;2H-Isoindole-2-acetic acid,3-dihydro-1,3-dioxo-.alpha.-(phenylmethyl)-, (S)-

Chemical Property of N-Phthaloyl-L-phenylalanine

Chemical Property:

• Vapor Pressure: 9.78E-11mmHg at 25°C
• Melting Point: 181-185 °C
• Refractive Index: -216.5 ° (C=2, EtOH)
• Boiling Point: 498 °C at 760 mmHg
• PKA: 3.50±0.10(Predicted)
• Flash Point: 255 °C
• PSA: 74.68000
• Density: 1.406 g/cm³
• LogP: 1.91640
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Soluble in methanol. (almost transparency)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 295.08445790
• Heavy Atom Count: 22
• Complexity: 445

Purity/Quality:

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

N-Phthaloyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N2C(=O)C3=CC=CC=C3C2=O
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)N2C(=O)C3=CC=CC=C3C2=O
• Uses: It is used as pharmaceutical intermediate.

Technology Process of N-Phthaloyl-L-phenylalanine

There total 31 articles about N-Phthaloyl-L-phenylalanine 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) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid (3588-64-5,5123-55-7,32150-90-6,38229-08-2)

Guidance literature:

for 0.05h; microwave irradiation;

Reference yield: 100.0%

L-phenylalanine hydrochloride (17585-69-2,27172-85-6,28069-46-7,74496-49-4,79541-99-4) + methyl 2-(N-succinimidyloxycarbonyl)benzoate (438470-19-0) → Nα-phthaloyl-L-phenylalanine (5123-55-7)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1021/jo016347h

Reference yield: 100.0%

C23H29NO4Si2 (1242459-38-6) → (R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid (3588-64-5,5123-55-7,32150-90-6,38229-08-2)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; 2.6-dimethylphenol; C₃₂H₁₂BF₂₄^(1-)*C₄₄H₃₀N₂O₂P⁽¹⁺⁾; In toluene; at -20 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja105945z

upstream raw materials:

phthalic anhydride

D-(R)-phenylalanine

C₂₃H₂₉NO₄Si₂

N-ethoxycarbonylphthalimide

Downstream raw materials:

(R)-2,2-dimethyl-3-(N,N-phthaloyl-L-phenylalanyl)-thiazolidine-4-carboxylic acid

benzoic acid-(N,N-phthaloyl-D-phenylalanine)-anhydride

N-(N,N-phthaloyl-L-phenylalanyl)-glycine ethyl ester

N-(N,N-phthaloyl-L-phenylalanyl)-L-phenylalanine-methyl ester

Refernces

• 1、 -. "AMINO ACID DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES". Page/Page column 46. . Retrieved 2020/08/13.
• 2、 Huang, Rizhen,Jing, Xiaoteng,Huang, Xiaochao,Pan, Yingming,Fang, Yilin,Liang, Guibin,Liao, Zhixin,Wang, Hengshan,Chen, Zhenfeng,Zhang, Ye. "Bifunctional Naphthoquinone Aromatic Amide-Oxime Derivatives Exert Combined Immunotherapeutic and Antitumor Effects through Simultaneous Targeting of Indoleamine-2,3-dioxygenase and Signal Transducer and Activator of Transcription 3". . p. 1544 - 1563. Retrieved 2020/03/10.