6349-98-0

Basic information

• Product Name: PHTHALYL-DL-GLUTAMIC ACID
• Synonyms: 2-PHTHALIMIDINO-GLUTARIC ACID;PHTHALOYL-DL-GLUTAMIC ACID;PHTHALYL-DL-GLUTAMIC ACID;PHT-DL-GLU-OH;N-PHTHALOYL-DL-GLUTAMIC ACID;2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)glutaric acid;N-Phthalimido-glutamicacid;2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid
• CAS NO: 6349-98-0
• Molecular Formula: C₁₃H₁₁NO₆
• Molecular Weight: 277.23
• EINECS: 228-754-8
• Mol File: 6349-98-0.mol

Chemical Properties

• Melting Point: 189.0 to 193.0 °C
• Boiling Point: 519.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.566±0.06 g/cm3(Predicted)
• Solubility: almost transparency in Methanol
• PKA: 3.45±0.10(Predicted)
• CAS DataBase Reference: PHTHALYL-DL-GLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PHTHALYL-DL-GLUTAMIC ACID(6349-98-0)
• EPA Substance Registry System: PHTHALYL-DL-GLUTAMIC ACID(6349-98-0)

Safety Data

• RTECS: MA3810000
• Hazardous Substances Data: 6349-98-0(Hazardous Substances Data)

Usage

Uses

2-Phthalimidino-glutaric acid is a stable analog of thalidomide.

InChI:InChI=1/C13H11NO6/c15-10(16)6-5-9(13(19)20)14-11(17)7-3-1-2-4-8(7)12(14)18/h1-4,9H,5-6H2,(H,15,16)(H,19,20)

Upstream product

• 85-44-9 phthalic anhydride 
• 56-86-0 L-glutamic acid 
• 100727-30-8 2-(cyclopent-2-en-1-yl)isoindoline-1,3-dione 
• 617-65-2 Glutamic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 3350-06-9 2-cyclopentenamine 
• 204922-61-2 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-nitro-pentanedioic acid 5-ethyl ester 1-methyl ester 
• 3343-28-0 N-phthaloylglutamic acid anhydride 

Downstream Products

• 617-65-2 Glutamic acid 
• 26577-32-2 EM 138 
• 222713-07-7 2-[1-(4-methoxybenzyl)-2,6-dioxopiperidin-3-yl]isoindoline-1,3-dione 
• 3343-28-0 N-phthaloylglutamic acid anhydride 
• 19117-51-2 2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)pentanedioyl dichloride 
• 26581-81-7 3-(1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione 
• 26840-61-9 1-benzyl-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione 
• 24666-53-3 2-(1-benzyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 94547-37-2 N⁵-benzyl-N²,N²-phthaloyl-glutamine 
• 222713-10-2 1-(4-methoxybenzyl)-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione 
• 222713-08-8 3-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-1-(4-methoxy-benzyl)-piperidine-2,6-dione 
• 222713-09-9 1-(4-methoxy-benzyl)-3-(1-oxo-3-phenylsulfanyl-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione 
• 600721-44-6 1-benzyloxy-3-(1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione 
• 600721-43-5 2-(1-benzyloxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 

Relevant articles and documents

Facile Synthesis of Thalidomide

We report a simple and facile procedure for the preparation of thalidomide in two steps with a high overall yield (56%). The preparation was composed of a reaction between anhydride phthalic and l-glutamic acid to form N-phthaloyl-dl-glutamic acid (IV), and a cyclization step using IV reacted with ammonium acetate in diphenyl ether to create thalidomide. Reaction parameters reaction time, temperature, solvent, and molar ratio of reagents in the procedure are optimized so that the reaction performance is highest while ensuring environmental friendliness. Moreover, this process has great potential for the industrial scale of thalidomide. These compounds were identified through IR, MS, 1H NMR, and 13C NMR.

Synthesis method of thalidomide

The invention relates to an industrial synthesis method of thalidomide, and specifically discloses a method, which comprises: directly synthesizing a crude product thalidomide by using phthalic anhydride and L-glutamic acid as raw materials through a two-step reaction one-pot method, and then carrying out refining purifying to obtain a finished product. According to the present invention, thalidomide is synthesized by using the two-step reaction one-pot method, microwave heating and other special equipment are not required, and the synthesis of the thalidomide anhydride intermediate is not required, such that the intermediate reaction process is eliminated, the use of acetic anhydride is avoided, the operation is simplified, the labor intensity is reduced, the production efficiency is improved, the environmental protection is achieved, and the method has high economic and social value.

Synthesis and evaluation of some N-Mannich bases of isoindole-1,3(2H)-dione derivatives as potential antimicrobial, anthelmintic and insecticidal agents

A series of some novel N-Mannich bases of benzimidazolyl substituted 1H-isoindole-1,3(2H) dione have been synthesized by cyclo-condensation of phthalic anhydride with different amino acids and thereafter, condensed with o-phenylenediamine following the Mannich protocol with different amines and formaldehyde to yield the titled compounds 5a-k. The structures of the newly synthesized compounds have been confirmed by FTIR, 1H NMR, mass spectral studies and elemental analyses. All the synthesized compounds have been evaluated for their in vitro antimicrobial, anthelmintic and insecticidal activities against selected microbes, helminthes and insects, compared to standard drugs streptomycin, nystatin, piperazine hydrochloride and cypermethrin respectively. Synthesized compounds 5d, 5j and 5k have shown promising activity against all selected microbes, helminthes and insects, while 5b is strongly toxic against S. aureus, 5g and 5k against B. subtilis, 5i against K. pneumoniae, 5a against T. viride and C. albicans, and 5h against A. niger. Compounds 5f, 5h, 5j, and 5k exhibited good antifungal activity, while 5b, 5g, 5e and 5i are sufficiently toxic for selected bacterial strains. Compounds 5a, 5b, 5c, 5e and 5f are strongly toxic against selected helminthes, while 5a, 5b, 5f, 5g, 5h and 5i have shown promising insecticidal activity.

Analogs of 2-Phthalimidinoglutaric acid

The invention provides new and useful analogs of 2-phthalimidinoglutaric acid. These analogs include DL-2-methyl-2-phthalimidinoglutaric acid and hydroxylated analogs of 2-phthalimidinoglutaric. The invention also provides processes for making these analogs. The invention also provides the two individual enantiomers of DL-2-methyl-2-phthalimidinoglutaric acid, (R)-(+)-2-methyl-2-phthalimidinoglutaric acid and (S)-(?)-2-methyl-2-phthalimidinoglutaric acid, and processes for separating these individual enantiomers from the racemate. Further, the invention provides methods for inhibiting angiogenesis and treating angiogenesis-associated diseases, including cancer and macular degeneration, by administering one or more of these compounds.

New synthetic routes to α-amino acids and γ-oxygenated α-amino acids. Reductive denitration and oxidative transformations of γ-nitro-α-amino acids

Transformation of γ-nitro-α-amino acid derivatives into α-amino acids by reductive denitration, into the γ-oxo-α-amino acids by ozonolysis of the corresponding amino acid ester nitronate derivatives, and into γ-hydroxy-α-amino acid derivatives by subsequent reduction of the oxo functionality, can be achieved in good yields. As the γ-nitro-α-amino acid derivatives are prepared from N,O-protected dehydroalanines derivable from the corresponding alanine, serine and cysteine derivatives by specific routes, the overall procedures provide a means for selective conversion of these simple α-amino acids into more complex ones.