Browse
Submit Data
Databases
API
Help

Dataset Information

13 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride.

ABSTRACT: We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1-4 h with yields up to 90%. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy.

SUBMITTER: George N

PROVIDER: S-EPMC7810210 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

A novel and highly efficient esterification process using triphenylphosphine oxide with oxalyl chloride.

Project description:Triphenylphosphine oxide (TPPO) and oxalyl chloride ((COCl)2) are used as novel and high-efficiency coupling reagents for the esterification of alcohols with carboxylic acids via the TPPO/(COCl)2 system at room temperature for 1?h. The reaction represents the first TPPO-promoted esterification under mild and neutral conditions with excellent yields. Furthermore, we proposed a plausible mechanism with the help of 31P NMR spectroscopy.

| S-EPMC5830786 | biostudies-literature

Enzymatic deprotection of the cephalosporin 3'-acetoxy group using Candida antarctica lipase B.

Project description:Cephalosporins remain one of the most important classes of antibiotics. A useful site for derivatization involves generation of and chemistry at the 3'-hydroxymethyl position. While 3'-acetoxymethyl-substituted cephalosporins are readily available, deacetylation to access the free 3'-hydroxymethyl group is problematic when the carboxylic acid is protected as an ester. Herein we report that this important transformation has been efficiently accomplished using Candida antarctica lipase B. Although this transformation is difficult to carry out using chemical methods, the enzymatic deacetylation has been successful on gram scale, when the cephalosporin is protected as either the benzhydryl or tert-butyl esters and on the corresponding sulfoxide and sulfone of the tert-butyl ester.

| S-EPMC2824665 | biostudies-literature

Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.

Project description:Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. A variety of aryl and aliphatic N-Boc-aldimines are effective substrates for this transformation. A preparative-scale reaction to deliver >90 mmol of product is shown using 1 mol % catalyst. The products of this transformation can be converted into several useful derivatives.

| S-EPMC3804837 | biostudies-literature

Iron Oxide-Cobalt Nanocatalyst for O-tert-Boc Protection and O-Arylation of Phenols.

Project description:Efficient and general protocols for the O-tert-boc protection and O-arylation of phenols were developed in this paper using a recyclable magnetic Fe?O?-Co?O? nanocatalyst (Nano-Fe-Co), which is easily accessible via simple wet impregnation techniques in aqueous mediums from inexpensive precursors. The results showed the catalysts were well characterized by XRD (X-ray Diffraction), ICP-AES (Inductive Coupled Plasma Atomic Emission Spectroscopy), TEM (Transmission Electron Microscopy), TOF-SIMS (Time-Of-Flight Secondary Ion Mass Spectrometry) and XPS (X-ray Photoelectron Spectroscopy). The O-tert-boc protection and O-arylation of phenols was accomplished in good to excellent yields (85–95%) and the catalyst was reusable and recyclable with no loss of catalytic activity for at least six repetitions.

| S-EPMC5923576 | biostudies-literature

Thorium-ligand multiple bonds via reductive deprotection of a trityl group.

Project description:Reaction of [Th(I)(NR2)3] (R = SiMe3) (2) with KECPh3 (E = O, S) affords the thorium chalcogenates, [Th(ECPh3)(NR2)3] (3, E = O; 4, E = S), in moderate yields. Reductive deprotection of the trityl group from 3 and 4 by reaction with KC8, in the presence of 18-crown-6, affords the thorium oxo complex, [K(18-crown-6)][Th(O)(NR2)3] (6), and the thorium sulphide complex, [K(18-crown-6)][Th(S)(NR2)3] (7), respectively. The natural bond orbital and quantum theory of atoms-in-molecules approaches are employed to explore the metal-ligand bonding in 6 and 7 and their uranium analogues, and in particular the relative roles of the actinide 5f and 6d orbitals.

| S-EPMC5707506 | biostudies-literature

Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group.

Project description:A trifluoroethyl (TFE) ether is specifically introduced as a protecting group in organic chemistry. Its first strategic application and removal in the total synthesis of vinigrol is discussed. Two lithium base mediated deprotection strategies for its removal are presented in this Letter. In one deprotection approach, the trifluoroethyl ether is converted to a difluorovinyl ether and then catalytically cleaved using osmium tetraoxide, while in the second approach a difluorovinyl anion is formed and trapped with an electrophilic oxygen reagent (MoOPH) to form a labile difluoroacetate. To further aid the reader, a summary of approaches for forming trifluoroethyl ethers is included as well as a discussion of alternate deprotection strategies.

| S-EPMC3878608 | biostudies-other

(tert-But-yl)(2-hy-droxy-eth-yl)ammonium chloride.

Project description:In the cation of the title mol-ecular salt, C6H16NO(+)·Cl(-), the N-C-C-O torsion angle is 176.5?(2)°. In the crystal, the cations and chloride ions are linked by N-H?O and O-H?O hydrogen bonds, generating a two-dimensional network parallel to (100).

| S-EPMC4120598 | biostudies-literature

Crystal structure of N-(tert-but-oxy-carbon-yl)phenyl-alanylde-hydro-alanine isopropyl ester (Boc-Phe-?Ala-OiPr).

Project description:In the title compound, the de-hydro-dipeptide (Boc-Phe-?Ala-OiPr, C20H28N2O5), the mol-ecule has a trans conformation of the N-methyl-amide group. The geometry of the de-hydro-alanine moiety is to some extent different from those usually found in simple peptides, indicating conjugation between the H2C=C group and the peptide bond. The bond angles around de-hydro-alanine have unusually high values due to the steric hindrance, the same inter-action influencing the slight distortion from planarity of the de-hydro-alanine. The mol-ecule is stabilized by intra-molecular inter-actions between the isopropyl group and the N atoms of the peptide main chain. In the crystal, an N-H?O hydrogen bond links the mol-ecules into ribbons, giving a herringbone head-to-head packing arrangement extending along the [100] direction. In the stacks, the mol-ecules are linked by weak C-H?O hydrogen-bonding associations.

| S-EPMC4257372 | biostudies-literature

1,3-Bis(4-tert-butyl-benz-yl)-4,5-dihydro-imidazolium chloride monohydrate.

Project description:In the title compound, C(25)H(35)N(2) (+)·Cl(-)·H(2)O, the imidazolidine ring adopts a twisted conformation, with a pseudo-twofold axis passing through the N-C-N carbon and the opposite C-C bond. The N-C-N fragment of the imidazolidine ring shows some degree of both double- and single-bond character due to partial electron delocalization. One of the tert-butyl groups is disordered over two conformations with occupancies of 0.714?(8) and 0.286?(8). In the crystal, O-H?Cl and C-H?O hydrogen bonds help to establish the packing.

| S-EPMC2968238 | biostudies-literature

Synthesis of Anti-Inflammatory Spirostene-Pyrazole Conjugates by a Consecutive Multicomponent Reaction of Diosgenin with Oxalyl Chloride, Arylalkynes and Hydrazines or Hydrazones.

Project description:Steroid sapogenin diosgenin is of significant interest due to its biological activity and synthetic application. A consecutive one-pot reaction of diosgenin, oxalyl chloride, arylacetylenes, and phenylhydrazine give rise to steroidal 1,3,5-trisubstituted pyrazoles (isolated yield 46-60%) when the Stephens-Castro reaction and heterocyclization steps were carried out by heating in benzene. When the cyclization step of alkyndione with phenylhydrazine was performed in 2-methoxyethanol at room temperature, steroidal α,β-alkynyl (E)- and (Z)-hydrazones were isolated along with 1,3,5-trisubstituted pyrazole and the isomeric 2,3,5-trisubstituted pyrazole. The consecutive reaction of diosgenin, oxalyl chloride, phenylacetylene and benzoic acid hydrazides efficiently forms steroidal 1-benzoyl-5-hydroxy-3-phenylpyrazolines. The structure of new compounds was unambiguously corroborated by comprehensive NMR spectroscopy, mass-spectrometry, and X-ray structure analyses. Performing the heterocyclization step of ynedione with hydrazine monohydrate in 2-methoxyethanol allowed the synthesis of 5-phenyl substituted steroidal pyrazole, which was found to exhibit high anti-inflammatory activity, comparable to that of diclofenac sodium, a commercial pain reliever. It was shown by molecular docking that the new derivatives are incorporated into the binding site of the protein Keap1 Kelch-domain by their alkynylhydrazone or pyrazole substituent with the formation of more non-covalent bonds and have higher affinity than the initial spirostene core.

| S-EPMC8746855 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data