101469-91-4

Basic information

• Product Name: N-Benzyl-(3S)-hydroxysuccinimide
• Synonyms: (3S)-N-Benzyl-3-hydroxypyrrolidine-2,5-dione;N-Benzyl-(3S)-hydroxysuccinimide;N-Benzyl-(S)-malimide;(S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione;(S)-1-benzyl-3-hydro×ypyrrolidine-2,5-dione;(R)-benzyl 3-fluoropyrrolidine-1-carboxylate
• CAS NO: 101469-91-4
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.20994
• EINECS: -0
• Mol File: 101469-91-4.mol

Chemical Properties

• Melting Point: 110-111℃
• Appearance: /
• Density: 1.385
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-Benzyl-(3S)-hydroxysuccinimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-(3S)-hydroxysuccinimide(101469-91-4)
• EPA Substance Registry System: N-Benzyl-(3S)-hydroxysuccinimide(101469-91-4)

Safety Data

• Hazardous Substances Data: 101469-91-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Benzyl-(3S)-hydroxysuccinimide is used as a mild and selective reagent for the bromination of alcohols and amines. Its reactivity with amines allows for the introduction of the succinimido group onto amines, making it a valuable tool in organic chemistry.
Used in Bioconjugation:
NBS is employed in bioconjugation reactions for the attachment of various functional groups to biomolecules, such as proteins and peptides. Its mild reaction conditions and selectivity for amines make it an ideal reagent for the formation of stable conjugates without affecting the biological activity of the target molecules.
Used in Peptide Synthesis:
In the field of peptide synthesis, N-Benzyl-(3S)-hydroxysuccinimide is used as a reagent for the introduction of the succinimido group onto amines during the synthesis process. This allows for the formation of stable peptide bonds and contributes to the overall efficiency and yield of the synthesis.
Used in Pharmaceutical Industry:
N-Benzyl-(3S)-hydroxysuccinimide is utilized in the development of pharmaceutical compounds, particularly in the synthesis of drug candidates and the modification of existing drugs to improve their pharmacological properties, such as solubility, stability, and bioavailability.
Used in Research and Development:
NBS is employed in research and development laboratories for the synthesis and modification of various chemical compounds, including the development of new materials, the study of chemical reactions, and the investigation of biological processes. Its versatility and reactivity make it a valuable tool for researchers in various scientific disciplines.

Upstream product

• 97-67-6 (S)-Malic acid 
• 100-46-9 benzylamine 
• 78027-57-3 (RS)-N-benzyl-3-hydroxypyrrolidine-2,5-dione 
• 173353-28-1 3-benzoyloxy-1-benzyl-2,5-pyrrolidinedione 
• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 

Downstream Products

• 101408-94-0 3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 101385-91-5 (S)-tert-butyl 3-acetoxypyrrolidine-1-carboxylate 
• 170711-05-4 (S)-1-benzyl-3-(benzyloxy)pyrrolidine-2,5-dione 
• 174684-58-3 (S)-1-benzyl-3-(tert-butyldimethylsilyloxy)pyrrolidine-2,5-dione 
• 886597-01-9 (S)-1-benzyl-3-[(tert-butyldimethylsilyl)oxy]-2,5-pyrrolidinedione 
• 935550-24-6 C₂₃H₂₉NO₄ 
• 935550-28-0 C₂₃H₂₉NO₄ 
• 935550-23-5 C₁₇H₂₁NO₄ 
• 935550-19-9 C₁₈H₂₃NO₄ 
• 935550-30-4 C₂₃H₃₅NO₄Si 
• 935550-25-7 C₂₃H₃₃NO₄Si 
• 935550-31-5 C₂₉H₄₃NO₄Si 
• 935550-21-3 C₂₄H₃₇NO₄Si 
• 192987-90-9 (4S)-1-benzyl-4,5-dihydroxypyrrolidin-2-one 

Relevant articles and documents

Synthesis method of (S)-3-pyrrolidinol hydrochloride

The invention discloses a synthesis method of (S)-3-pyrrolidinol hydrochloride, which belongs to the field of drug synthesis, and comprises the following steps: dehydrating and amidating L-malic acidand benzylamine as raw materials to obtain (3S)-N-benzyl-3-hydroxypyrrolidine-2,5-diketone, and carrying out one-pot reduction, debenzylation and salification to synthesize (S)-3-pyrrolidinol hydrochloride. The method is short in synthetic route, simple to operate, high in yield, good in product purity and beneficial to industrial production.

Substituted pyrazolo[1,5-a]pyrimidine compound and pharmaceutical composition and application thereof

The invention provides a pharmaceutical composition and application of a substituted pyrazolo[1,5-a]pyrimidine compound. The substituted pyrazolo[1,5-a]pyrimidine compound is a compound shows as the formula (I) (please see the specifications for the formula), or pharmaceutically acceptable salt, prodrug, hydrate or solvent compound, polymorphism, stereisomer or isotope variant of the substituted pyrazolo[1,5-a]pyrimidine compound. The substituted pyrazolo[1,5-a]pyrimidine compound can be used for treating diseases which can be treated through a Trk kinase inhibitor.

COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY

Provided are indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which LRRK2 kinase is involved. Also provided are pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which LRRK2 kinase is involved.

COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY

The present invention is directed to indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which the LRRK2 kinase is involved, such as Parkinson's Disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which LRRK-2 kinase is involved.

COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY

Disclosed are indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which LRRK2 kinase is involved. Also disclosed are pharmaceutical compositions in the prevention or treatment of such diseases in which LRRK2 kinase is involved.

COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY

The present invention is directed to indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which the LRRK2 kinase is involved, such as Parkinson's Disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which LRRK-2 kinase is involved.

3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: Inhibition of rat intestinal α-glucosidase

Thirteen pyrrolidine-based iminosugar derivatives have been synthesized and evaluated for inhibition of α-glucosidase from rat intestine. The compounds studied were the non-hydroxy, mono-hydroxy and dihydroxypyrrolidines. All the compounds were N-benzylated apart from one. Four of the compounds had a carbonyl group in the 2,5-position of the pyrrolidine ring. The most promising iminosugar was the trans-3,4-dihydroxypyrrolidine 5 giving an IC50 of 2.97 ± 0.046 and a KI of 1.18 mM. Kinetic studies showed that the inhibition was of the mixed type, but predominantly competitive for all the compounds tested. Toxicological assay results showed that the compounds have low toxicity. Docking studies showed that all the compounds occupy the same region as the DNJ inhibitor on the enzyme binding site with the most active compounds establishing similar interactions with key residues. Our studies suggest that a rotation of ～90° of some compounds inside the binding pocket is responsible for the complete loss of inhibitory activity. Despite the fact that activity was found only in the mM range, these compounds have served as simple molecular tools for probing the structural features of the enzyme, so that inhibition can be improved in further studies.

Synthesis of novel enantiopure ionic liquids from (S)-malic acid

A straightforward and practical synthesis of six novel pyrrolidinium salts based on (S)-malic acid is reported. Two of them were liquid at room temperature, and can be employed as novel chiral ionic liquids for enantioselective applications.ARKAT-USA, Inc.

A study on the racemization step in the synthesis of pyrrolidinols via cyclic α-hydroxyimides

Analytical HPLC methods for the determination of the enantiomeric excess of N-protected malimides 1 as well as the corresponding pyrrolidinol 5 and tartarimides 2 and 3 have been established. On this basis, a study to reveal the racemization step in the synthesis of pyrrolidinols from α-hydroxyacids, via chiral cyclic α-hydroxyimides, has been undertaken. It was confirmed that the known, one-step method for the synthesis of the N-protected chiral cyclic imides from α-hydroxydiacids proceeded with little racemization, and partial racemization has been proven to occur during the reduction of the resultant imide 1a with LAH to yield the corresponding pyrrolidinol 5. Conditions have been defined in order to avoid racemization in the LAH reduction step.

PROCESS FOR PREPARING 3-SUBSTITUTED PYRROLIDINE COMPOUNDS

Disclosed is a process for preparing 3 -substituted pyrrolidine compounds of formula (VII) or salts thereof, wherein R1 is described herein, which are intermediate compounds useful for the synthesis of darifenacin which is indicated for the treatment of overactive bladder with symptoms of urge, urinary incontinence, and the like, and pharmaceutically acceptable salts thereof. Also disclosed is a process for preparing darifenacin and pharmaceutically acceptable salts thereof.