High-Temperature Boc Deprotection in Flow and Its Application in Multistep Reaction Sequences.

Org Lett

Discovery Chemistry and Technologies, AbbVie, Inc., 1 North Waukegan Road, North Chicago, Illinois 60064, United States.

Published: April 2016

A simplified Boc deprotection using a high-temperature flow reactor is described. The system afforded the qualitative yield of a wide variety of deprotected substrates within minutes using acetonitrile as the solvent and without the use of acidic conditions or additional workups. Highly efficient, multistep reaction sequences in flow are also demonstrated wherein no extraction or isolation was required between steps.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.6b00378DOI Listing

Publication Analysis

Top Keywords

boc deprotection
8
multistep reaction
8
reaction sequences
8
high-temperature boc
4
deprotection flow
4
flow application
4
application multistep
4
sequences simplified
4
simplified boc
4
deprotection high-temperature
4

Similar Publications

A series of 3-phosphonyl polysubstituted pyridine were first synthesized by photocatalysis, combining a phosphonyl radical cascade reaction, Boc deprotection, and aromatization. This strategy can avoid the difficulties of activating the C3-H bond on pyridine to synthesize 3-phosphonylpyridine under mild conditions. Furthermore, by constructing different enynes, we can achieve the metal-free modular synthesis of 3-phosphonyl polysubstituted pyridine, which will be transferred into a new type of phosphine ligand.

View Article and Find Full Text PDF

One of the grand challenges in chemical biology is identifying a small-molecule modulator for all proteins within a proteome. To expand the variety and number of ligandable proteins for drug discovery, the objective of this study was to synthesize and evaluate the protein target profiles of electrophilic and photoreactive fully functionalized small-molecule probes (FFSMPs) featuring increased scaffold-, appendage-, and protein-reactive functional group (PRFG) diversity. FFSMPs contain: (1) a protein-binding motif, (2) an electrophilic or photoreactive PRFG for target protein capture, and (3) a terminal alkyne for click chemistry-based proteomic applications.

View Article and Find Full Text PDF

Primary Amine-Functionalized Chiral Covalent Organic Framework Enables High-Efficiency Asymmetric Catalysis in Water.

ACS Appl Mater Interfaces

October 2024

GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, and Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006, P. R. China.

Aqueous asymmetric catalysis using chiral covalent organic frameworks (COFs) represents a significant advancement but remains to be explored. Herein, we present the first example of aqueous asymmetric catalysis catalyzed by a primary amine-tagged chiral -ADP-TAPB COF. The -ADP-TAPB COF was synthesized by the postsynthetic deprotection of -ADP-TAPB-Boc bearing a protective tert-butoxycarbonyl (Boc) group, which was constructed by a Schiff-base reaction between an alanine-derived chiral building block (-ADP-Boc) and 1,3,5-tris(4-aminophenyl)benzene (TAPB).

View Article and Find Full Text PDF

An efficient regioconvergent synthesis of 3-aza-obeticholic acid.

Steroids

December 2024

Ferrier Research Institute, Victoria University of Wellington, 69 Gracefield Rd, Lower Hutt 5040, New Zealand. Electronic address:

Bile acids (BAs) are steroidal molecules that play important roles in nutrient absorption, distribution, and excretion. They also act on specific receptors implicated in various metabolic and inflammatory diseases demonstrating their importance as potential drug candidates. Accordingly, there has been a concerted effort to develop new BA derivatives to probe structure-activity relationships with the goal of discovering BA analogues with enhanced pharmacological properties.

View Article and Find Full Text PDF

Mechanochemical deprotection of -butoxycarbonyl (Boc) group using basic alumina.

Org Biomol Chem

October 2024

Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, 312000, China.

A solvent-free, operationally simple, and chemoselective mechanochemical method for -butoxycarbonyl (Boc) deprotection is described. In a planetary ball mill, -Boc groups from protected heterocycles, amides, and anilines, as well as -Boc groups from carbonates, can be removed selectively, using basic alumina. This high-yielding protocol avoids tedious extraction and column chromatography.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!