134953-64-3

Upstream product

• 1113-78-6 tri(sec-butyl)borane 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 33966-50-6 SEC-BUTYLAMINE 
• 24424-99-5 di-tert-butyl dicarbonate 
• 41839-96-7 N-(tert-butoxycarbonyl)-succinimide 
• 598-30-1 sec.-butyllithium 
• 150884-56-3 N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 66389-76-2 tert-butyl methyl iminodicarboxylate 
• 105838-14-0 tert-butyl N-tosyloxycarbamate 

Relevant academic research and scientific papers

A convenient synthesis of N-boc protected primary amines via the reaction of organoboranes with Li or K t-butyl-N-tosyloxycarbamate

Primary and secondary alkylboranes reacted rapidly at low temperature with Li or K t-butyl-N-tosyloxycarbamate (LiBTOC or KBTOC) to give the corresponding N-Boc protected primary amines in modest to good yields (16-81%).

Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate

The sulfated polyborate catalyzed an efficient and chemoselective N-tert-butyloxycarbonylation of amines under ultrasonic irradiation is developed. A broad substrate scope has been demonstrated for N-Boc protection of various primary/secondary amines. It allows converting several aliphatic/aryl/heteroaryl amines, amino alcohol, aminoester, and chiral amines to their N-Boc-protected derivatives under solvent-free conditions with excellent yields. The protocol has several advantages such as easy catalyst, and product isolation, short reaction time, excellent yields, outstanding chemoselectivity, and catalyst recyclability, among others. This makes the process practicable, economical, and environmentally benign.

Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions

Nanocerium oxide mediated an efficient and green protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at ambient temperature. Various aliphatic, aromatic and heteroaromatic amines were protected using developed protocol and several functional groups such as alcohol, phenol and ester were well tolerated under these conditions. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Lead Optimization of Benzoxazolone Carboxamides as Orally Bioavailable and CNS Penetrant Acid Ceramidase Inhibitors

Sphingolipids (SphLs) are a diverse class of molecules that are regulated by a complex network of enzymatic pathways. A disturbance in these pathways leads to lipid accumulation and initiation of several SphL-related disorders. Acid ceramidase is one of the key enzymes that regulate the metabolism of ceramides and glycosphingolipids, which are important members of the SphL family. Herein, we describe the lead optimization studies of benzoxazolone carboxamides resulting in piperidine 22m, where we demonstrated target engagement in two animal models of neuropathic lysosomal storage diseases (LSDs), Gaucher's and Krabbe's diseases. After daily intraperitoneal administration at 90 mg kg-1, 22m significantly reduced the brain levels of the toxic lipids glucosylsphingosine (GluSph) in 4L;C? mice and galactosylsphingosine (GalSph) in Twitcher mice. We believe that 22m is a lead molecule that can be further developed for the correction of severe neurological LSDs where GluSph or GalSph play a significant role in disease pathogenesis.

Synthesis, X-ray crystallography, and reactions of N-acyl and N-carbamoyl succinimides

A collection of N-acyl and N-carbamoyl succinimides were prepared by acylation of succinimide with acyl chlorides or by ethylene dichloride (EDC) coupling of carboxylic acids. The x-ray crystal structures of N-benzoyl and N-p-nitrobenzoyl succinimides were determined. The N-acyl succinimides were effective in acylating primary amines, a secondary amine, and an aromatic amine. Copyright

Electrophilic amination of diorganozinc reagents by oxaziridines

Electrophilic amination of organozinc reagents by oxaziridines has been studied. Diorganozinc reagents R2Zn (R = alkyl or aryl) react with N-Boc oxaziridine to afford N-Boc protected primary amines BocNHR in moderate to good yields. No additive

An expedient transformation of alcohols into N-Boc-amines

t-Butyl methyl iminodicarbonate (3) can be easily alkylated with primary or secondary alcohols under Mitsunobu conditions (DIAD, TPP) to give the corresponding N-alkyl iminodicarbonates. Partial deprotection of the latter with methanolic potassium hydroxi

Electrophilic amination of carbanions with metallated t-butyl N-tosyloxycarbamate

The reactivity of metallated t-butyl N-tosyloxycarbamate as electrophilic aminating reagent was studied.N-Boc-protected primary alkyl and aryl amines were obtained by reaction of organometallic derivatives with this reagent. - Keywords: electrophilic amin

Electrophilic amination: First direct transfer of NHBoc with Li t-butyl-N-tosyloxycarbamate

Lithium t-butyl-N-tosyloxycarbamate (LiBTOC) has been found to be an electrophilic aminating reagent. This species reacts with organometallic reagents, ester enolates and α-cuprophosphonates to provide primary amines as well as α-aminocarboxylic and phosphonic esters in their N-(Boc) protected form. (35-80% isolated yields).