N-Phthaloyl-L-glutamine

Base Information

• Chemical Name: N-Phthaloyl-L-glutamine
• CAS No.: 3343-29-1
• Molecular Formula: C13H12 N2 O5
• Molecular Weight: 276.249
• Hs Code.: 2925190090
• NSC Number: 88735
• DSSTox Substance ID: DTXSID30955059
• Nikkaji Number: J2.440.233I
• Wikidata: Q82934521
• Mol file: 3343-29-1.mol

Synonyms:3343-29-1;N-alpha-Phthalyl-L-glutamine;N-Phthaloyl-L-glutamine;(S)-5-Amino-2-(1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid;N-Phthalylglutamine;(s)-4-carbamoyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid;(2S)-5-amino-2-(1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid;NSC 88735;N-Phthalyl-L-glutamine;phthalyl-l-glutamine;N-Phthalyl-D,L-glutamine;N-Phthalyl-DL-glutamin [German];MFCD00190993;s-pign;Glutaramic acid, 2-phthalimido-, L-;N-phthalyl-l-glutamin;N-Phthalyl-DL-glutamin;n-a-phthalyl-l-glutamine;SCHEMBL442029;Glutaramic acid, 2-phthalimido-;DTXSID30955059;2H-Isoindole-2-acetic acid, alpha-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-, (S)-;NSC88735;NSC-88735;AKOS015967133;AC-29912;AS-35406;CS-0149729;Glutaramic acid, 2-phthalimido-, L- (8CI);2H-Isoindole-2-acetic acid,3-dihydro-1,3-dioxo-, (S)-;2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-hydroxy-5-iminopentanoic acid;2H-Isoindole-2-acetic acid, .alpha.-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-, (S)-

Chemical Property of N-Phthaloyl-L-glutamine

Chemical Property:

• Vapor Pressure: 3.27E-15mmHg at 25°C
• Melting Point: 163 °C
• Boiling Point: 599.3°Cat760mmHg
• PKA: 3.47±0.10(Predicted)
• Flash Point: 316.3°C
• PSA: 117.77000
• Density: 1.508g/cm³
• LogP: 0.63950
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 276.07462149
• Heavy Atom Count: 20
• Complexity: 438

Purity/Quality:

98%min ^*data from raw suppliers

N-α-Phthalyl-L-glutamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A reproductive hazard.
• Hazard Codes: A reproductive hazard.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)C(CCC(=O)N)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)[C@@H](CCC(=O)N)C(=O)O

Technology Process of N-Phthaloyl-L-glutamine

There total 5 articles about N-Phthaloyl-L-glutamine 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: 72.0%

phthalic anhydride (85-44-9) + L-glutamine (56-85-9,26700-71-0) → (S)-2-phthalimidoglutaramic acid (3343-29-1,2110-19-2,174591-46-9)

Guidance literature:

phthalic anhydride; L-glutamine; In N,N-dimethyl-formamide; at 90 - 95 ℃; for 3h;

With hydrogenchloride; water; at 15 ℃; for 2h; pH=1.2;

Reference yield: 67.0%

L-glutamine (56-85-9,26700-71-0) + N-ethoxycarbonylphthalimide (22509-74-6) → (S)-2-phthalimidoglutaramic acid (3343-29-1,2110-19-2,174591-46-9)

Guidance literature:

L-glutamine; N-ethoxycarbonylphthalimide; With sodium carbonate; In water; for 1h; Inert atmosphere;

With hydrogenchloride; In water; for 1h;

DOI:10.1021/op980201b

Reference yield:

(S)-thalidomide (841-67-8) → (S)-4-phthalimidoglutaramic acid (2614-08-6,2820-40-8) + (R)-thalidomide (2614-06-4) + α-(o-carboxybenzamido)-L-glutarimide (131-68-0,29883-18-9) + (S)-2-phthalimidoglutaramic acid (3343-29-1,2110-19-2,174591-46-9)

Guidance literature:

human serum albumin; In phosphate buffer; at 37 ℃; pH=7.40; Further Variations:; Catalysts; catalyst, buffer concentration; Kinetics;

DOI:10.1021/tx9801817

upstream raw materials:

N-phthaloyl-L-glutamic anhydride

(S)-thalidomide

phthalic anhydride

L-glutamine

Downstream raw materials:

thalidomide

L-Tryptophan

Refernces

• 1、 -. "PROCESSES FOR THE PREPARATION OF THALIDOMIDE". Page/Page column 12-15. . Retrieved 2009/08/14.
• 2、 Muller, George W.,Konnecke, William E.,Smith, Alison M.,Khetani, Vikram D.. "A concise two-step synthesis of thalidomide". . p. 139 - 140. Retrieved 2013/09/08.