179915-11-8

Basic information

• Product Name: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE
• Synonyms: (R)-benzyl 2,6-dioxopiperidin-3-ylcarbamate;REF DUPL: R-3-N-Cbz-amino-2,6-Dioxo-piperidine;Carbamic acid, [(3R)-2,6-dioxo-3-piperidinyl]-, phenylmethyl ester (9CI);benzyl N-[(3R)-2,6-dioxopiperidin-3-yl]carbamate;(R)-3-Cbz-amino-2,6-dioxopiperidine
• CAS NO: 179915-11-8
• Molecular Formula: C13H14N2O4
• Molecular Weight: 262.26
• Mol File: 179915-11-8.mol

Chemical Properties

• Boiling Point: 520.2°Cat760mmHg
• Flash Point: 268.4°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 6.37E-11mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.58±0.20(Predicted)
• CAS DataBase Reference: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE(179915-11-8)
• EPA Substance Registry System: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE(179915-11-8)

Safety Data

• Hazardous Substances Data: 179915-11-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Synthesis:
(R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE is used as a building block for the creation of various drugs and drug candidates due to its chemical versatility and the ability to be selectively deprotected to facilitate further reactions. Its structural features, including the piperidine ring and ketone groups, make it suitable for the synthesis of diverse bioactive compounds, contributing to the development of new medications for a variety of therapeutic purposes.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE is employed as a key intermediate in the synthesis of complex organic molecules with potential pharmaceutical applications. Its unique structure allows for the exploration of novel chemical space and the optimization of drug candidates with improved potency, selectivity, and pharmacokinetic properties.
Used in Drug Development:
(R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE is utilized in the development of new medications for a variety of therapeutic areas, including but not limited to, central nervous system disorders, cardiovascular diseases, metabolic disorders, and oncology. Its potential in these areas is attributed to its ability to be modified and incorporated into diverse chemical scaffolds, leading to the discovery of innovative therapeutic agents with improved efficacy and safety profiles.

InChI:InChI=1/C13H14N2O4/c16-11-7-6-10(12(17)15-11)14-13(18)19-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,18)(H,15,16,17)/t10-/m1/s1

Upstream product

• 67-56-1 methanol 
• 2650-64-8 Cbz-L-Gln 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 13139-52-1 N-carbobenzoxy-D-glutamine 
• 56-85-9 L-glutamine 
• 501-53-1 benzyl chloroformate 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 56-86-0 L-glutamic acid 
• 50516-14-8 Nα-benzyloxycarbonyl-glutamine 
• 13907-82-9 N²-benzyloxycarbonyl-L-glutamine methyl ester 

Downstream Products

• 673485-72-8 (3R)-3-aminohexahydro-2,6-pyridinedione 
• 827026-45-9 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione 
• 73839-06-2 3-amino-3-methyl-piperidine-2,6-dione hydrochloride 
• 191732-76-0 2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione 
• 55003-81-1 2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione 
• 90802-45-2 DL-3-amino-2,6-piperidinone hydrobromide 
• 202271-89-4 (R)-(+)-4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3-dione 
• 202271-89-4 (S)-(-)-4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3-dione 
• 1314881-81-6 padanamide B 
• 1426657-05-7 C₃₇H₆₀N₆O₉Si 
• 29883-25-8 (S)-3-aminopiperidine-2,6-dione 

Relevant articles and documents

Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity

A thalidomide-binding aptamer was produced by systematic evolution of ligands by exponential enrichment from a library of non-natural DNA in which thymidine had been replaced with a modified deoxyuridine bearing a cationic functional group via a hydrophobic methylene linker at the C5 position. The additional functional group in the modified DNA aptamer could improve stability against nucleases and increase the binding affinity to thalidomide. The selected aptamer could recognize thalidomide enantioselectively, although a racemic thalidomide-attached gel was used for the selection. Surface plasmon resonance and fluorescence titration studies revealed that the selected modified DNA aptamer and a truncated version bound with an (R)-thalidomide derivative with high enantioselectivity, but not with the (S)-form. The modified group in the DNA aptamer is indispensable for the interaction with thalidomide, as the corresponding natural type DNA bearing the same base sequence showed no binding affinity with (R)-nor (S)-thalidomide. Computational sequence analysis suggested that the selected apatamer (108mer) could fold into a three-way junction structure; however, truncation of this aptamer (31 mer) revealed that the thalidomide-binding site is a hairpin-bulge region that is a component of one of the arms of the three-way junction structure. The Kd value of the truncated 31 mer aptamer for binding with the (R)-thalidomide derivative was 1.0 μM estimated from fluorescence titration study. The aptamer that can recognize a single enantiomer of thalidomide will be useful as a biochemical tool for the analysis and study of the biological action of thalidomide enantiomers.

Preparation method of lenadomide

The invention discloses a preparation method of lenalidomide, and belongs to the field of organic synthesis. 2-methyl-3-methyl nitrobenzoate and 3-N-benzyloxy-carbonyl-L-glutamine serve as starting materials, and an important intermediate 2-brooethyl-3-methyl nitrobenzoate is obtained through a bromination reaction of 2-methyl-3-methyl nitrobenzoate. 3-N-benzyloxy-carbonyl-L-glutamine is cyclizedunder catalysis to produce 3-N-benzyloxy-carbonyl-2,6-dioxopiperidine, an amino group is subjected to deprotection to produce 3-amino-2,6-piperidone halide, 3-(4-nitro-1-oxo-1,3-o-xylylenimine-2-yl)piperidine-2,6-diketone is obtained through an aminolysis reaction of 3-N-benzyloxy-carbonyl-2,6-dioxopiperidine and 2-brooethyl-3-methyl nitrobenzoate, and then lenalidomide is prepared through reduction. The method has the advantages that the cost of raw materials are low, aftertreatment is simple, and the yield is high, and the production cost of the lenalidomide as a bulk drug is greatly reduced. The method is a convenient and efficient lenalidomide synthesis method suitable for industrial production.

PROCESS FOR THE PREPARATION OF POMALIDOMIDE

The present invention relates to a process for the preparation of pomalidomide. The present invention also provides a process for the preparation of 2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione, a compound of Formula II and its use for the preparation of pomalidomide. The pomalidomide may be made having a yield greater than 97% and the 2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione (Formula II) may be made having a yield greater than 88%.

A method for the preparation of amine to that (by machine translation)

The invention discloses a method for the preparation of amine to that, the specific step includes: to 2 - methyl - 3 - nitro benzoic acid as the raw material, to obtain 2 - bromomethyl - 3 - nitro-benzoic acid methyl ester; L - glutamic acid as the raw material to make the N - CBZ - L - glutamic acid; to N - CBZ - L - glutamic acid as the raw material to make the 3 - amino - 2, 6 - piperidine dione hydrochloride; to 2 - methyl - 3 - nitro-benzoic acid methyl ester with 3 - amino - 2, 6 - piperidine dione hydrochloride as the raw material to make the 3 - (4 - nitro - 1, 3 dihydro - 1 - oxo - 2 hydrogen - isoindol - 2 - yl) piperidine - 2, 6 - dione; to 3 - (4 - nitro - 1, 3 dihydro - 1 - oxo - 2 hydrogen - isoindol - 2 - yl) piperidine - 2, 6 - dione as raw materials to that amine. The method of the invention has simple technological process, raw material economic, few by-products, and purification is simple, high yield, environment-friendly and the like, after treatment is simple, has better practicability and application value, has great industrial prospects. (by machine translation)

Preparation method of deuterated intermediate

The present invention provides a preparation method of a deuterated intermediate. The deuterated intermediate has a structure shown by a formula I; the preparation method comprises the following steps: amino groups in a raw material A and an aldehyde grou

Methods for the treatment of cancer and inflammatory diseases using cereblon as a predictor

Uses of the protein cereblon as a predictor of clinical sensitivity to cancer, inflammatory diseases, and patient response to drug treatment.

METHODS FOR THE TREATMENT OF LOCALLY ADVANCED BREAST CANCER

Provided herein are methods of treating, preventing and/or managing locally advanced breast cancer, including inflammatory breast cancer, which comprise administering to a patient one or more immunomodulatory compounds or enantiomers or mixtures of enantiomers thereof, or pharmaceutically acceptable salts, solvates, hydrates, co-crystals, clathrates, or polymorphs thereof.

PROCESS FOR LENALIDOMIDE

The present invention provides an improved process for the preparation of 3-(benzyloxycarbonylamino)piperidine-2,6-dione. The present invention also provides an improved process for the preparation of 3-(4-nitro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione. The present invention further provides a process for the preparation of lenalidomide crystalline Form H1.

Total synthesis of padanamides A and B

The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures. The Royal Society of Chemistry.

Synthesis of (-)-julocrotine and a diversity oriented Ugi-approach to analogues and probes

An improved total synthesis of (-)-julocrotine in three steps from Cbz-glutamine, in 51% overall yield, is presented. To demonstrate the potential of the heterocyclic moiety for diversity oriented synthesis, a series of (-)-julocrotine analogues was synthesized by employing the heterocyclic precursor as an amino input in Ugi four-component reactions (Ugi-4CR) [1].