174591-46-9

Basic information

• Product Name: (R)-2-phthalimidoglutaramic acid
• CAS NO: 174591-46-9
• Molecular Weight: 276.249
• Mol File: 174591-46-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 599.3±45.0 °C(Predicted)
• Density: 1.508±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-2-phthalimidoglutaramic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-phthalimidoglutaramic acid(174591-46-9)
• EPA Substance Registry System: (R)-2-phthalimidoglutaramic acid(174591-46-9)

Safety Data

• Hazardous Substances Data: 174591-46-9(Hazardous Substances Data)

Usage

Description

(R)-2-phthalimidoglutaramic acid, with the molecular formula C12H10N2O5, is an organic compound featuring a phthalimide group and a glutaric acid moiety. As a chiral molecule, it has a non-superimposable mirror image and exists in two enantiomeric forms, with (R)-2-phthalimidoglutaramic acid being one of them. (R)-2-phthalimidoglutaramic acid is widely recognized for its utility as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Moreover, it has demonstrated potential biological activity, making it a subject of interest for its possible application as a drug candidate in various medical fields.

Uses

Used in Pharmaceutical Synthesis:
(R)-2-phthalimidoglutaramic acid is used as a key building block for the synthesis of various pharmaceuticals. Its unique structure allows for the creation of a diverse range of compounds with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, (R)-2-phthalimidoglutaramic acid is utilized as a crucial component in the development of new compounds designed to enhance crop protection and improve agricultural productivity.
Used in Organic Chemistry:
(R)-2-phthalimidoglutaramic acid serves as an important intermediate in organic chemistry, facilitating the synthesis of a wide array of organic compounds with diverse applications.
Used in Drug Development:
Due to its demonstrated biological activity, (R)-2-phthalimidoglutaramic acid is being investigated for its potential as a drug candidate. Its unique properties make it a promising starting point for the development of new medications to address various medical conditions.

Upstream product

• 56-85-9 GLUTAMINE 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 85-44-9 phthalic anhydride 
• 56-85-9 L-glutamine 
• 88-95-9 Phthaloyl dichloride 
• 6349-98-0 N-phthalylglutamic acid 
• 2614-06-4 (R)-thalidomide 
• 841-67-8 (S)-thalidomide 
• 3343-28-0 N-phthaloylglutamic acid anhydride 
• 25830-77-7 N-phthaloyl-L-glutamic anhydride 

Relevant articles and documents

Radiosynthesis of 13N-labeled thalidomide using no-carrier-added [13N]NH3

Recent studies revealed that thalidomide (1) has unique and broad pharmacological effects on multi-targets although the application of 1 in therapy is still controversial. In this study, we synthesized nitrogen-13-labeled thalidomide ([13N]1) as a potential positron emission tomography (PET) probe using no-carrier-added [13N]NH 3 as a labeling agent. By use of an automated system, [ 13N]1 was prepared by reacting N-phthaloylglutamic anhydride (2) with [13N]NH3, following by cyclization with carbonyldiimidazole in a radiochemical yield of 56±12% (based on [ 11N]NH3, corrected for decay) and specific activity of 49±24GBq/μmol at the end of synthesis (EOS). At EOS, 570-780MBq (n=7) of [13N]1 was obtained at a beam current of 15 μA after 15 min proton bombardment with a synthesis time of 14 min from the end of bombardment. Using a small animal PET scanner, preliminary biodistribution of [ 13N]1 in mice was examined. Copyright

A concise two-step synthesis of thalidomide

A two-step synthesis of thalidomide is presented. The sequence requires no purifications. Treatment of L-glutamine with N-carbethoxyphthalimide produces N-phthaloyl-L-glutamine. Cyclization of N-phthaloyl-L-glutamine to afford thalidomide is accomplished by treatment with CDI in the presence of a catalytic amount of DMAP.

PROCESSES FOR THE PREPARATION OF THALIDOMIDE

The present invention provides a process for the preparation of thalidomide (I) comprising: i) reacting a compound of formula (II), where one of R represents -OH or -NH2 and the other of R represents -NH2 or -OH, respectively, with a phthaloylating agent in the presence of a base and a a non-polar organic solvent to obtain a phthaloyl derivative where R have the same meanings as above; and ii) dehydrating the phthaloyl derivative using a dehydrating agent selected from an acid anhydride, an acid halide, an ion exchange resin or a molecular sleve to obtain thalidomide (I).