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Enantioselective synthesis of (3R)- and (3S)-piperazic acids. The comparative unimportance of DMPU mediated retro-hydrazination

In response to a recent literature report by Decicco and Leathers, the work of Hale, Delisser, and Manaviazar (1992) on the asymmetric synthesis of (3R)- and (3S)-piperazic acids has been reinvestigated, and the originally claimed product yields fully substantiated. The claims made in reference 13 about the proportions of cyclised product 6 and starting bromide 20 isolated from the low temperature electrophilic hydrazination-nucleophilic cyclisation of 20 with di-t-butylazodicarboxylate (DBAD) and DMPU as an additive are inaccurate. The retro-hydrazination reaction that they claim is problematic when DMPU is added to the hydrazinated reaction mixture has been demonstrated not to have a seriously detrimental effect on cyclisation product yield and to be unimportant. The other main ion of reference 13, that the electrophilic hydrazination and nucleophilic cyclisation of 20 gives 6 in 91% isolated yield when n-Bu4NI is employed as an additive (instead of DMPU) has also been shown to be in error. We have carefully repeated a scaled-down version of the n-Bu4NI catalysed procedure and have found that 6 is generally isolated in yields of 50-56% after flash chromatography. We have concluded that n-Bu4NI does not significantly increase the yields of cyclisation products 6 or 17 when it is employed as a cyclisation additive. Herein, we report details of our two preferred ‘crude’ experimental procedures for preparing the enantiomers of piperazic acid in high optical purity, neither of which requires chromatographic purification of the reaction intermediates en route. Both these preferred ‘crude’ methods for preparing 11 and 19 have been consistently reproduced many times in these laboratories over the past few years. In our view, they remain the most expedient and highest yielding methods currently available for obtaining 11 and 19 in high optical purity.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2160NO – PubChem

 

Brief introduction of 102029-44-7

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Directed orthometalation and the asymmetric total synthesis of N -deoxymilitarinone A and torrubiellone B

A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1801NO – PubChem

 

The Absolute Best Science Experiment for (S)-N-Boc-2,2-dimethyloxazolidine-4-carboxylic Acid

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COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS

The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2361NO – PubChem

 

Can You Really Do Chemisty Experiments About Oxazolidin-2-one

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A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional beta- and gamma-lactams, can be employed.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H283NO – PubChem

 

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Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines

The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H281NO – PubChem

 

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A practical and effective ruthenium trichloride-based protocol for the regio- and stereoselective catalytic hydroamidation of terminal alkynes

A rational catalyst development based on mechanistic and spectroscopic investigations led to the discovery of a new protocol for catalytic hydroamidation reactions that draws on easily available ruthenium trichloride trihydrate (RuCl3·3H2O) as the catalyst precursor instead of the previously employed, expensive bis(2-methylallyl)(1,5- cyclooctadiene) ruthenium(II). This practical and easy-to-use protocol dramatically improves the synthetic applicability of Ru-catalyzed hydroamidations. The catalyst, generated in situ from ruthenium(III) chloride hydrate, tri-n-butylphosphine, 4-(dimethylamino)-pyridine and potassium carbonate, effectively promotes the addition of secondary amides, lactams and carbamates to terminal alkynes under formation of (E)-anti-Markovnikov enamides. The scope of the new protocol is demonstrated by the synthesis of 24 functionalized enamide derivatives, among them valuable intermediates for organic synthesis.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H563NO – PubChem

 

Brief introduction of Oxazolidin-2-one

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IMIDAZOPYRAZINES AS LSD1 INHIBITORS

The present invention is directed to imidazo[1,2-a]pyrazine derivatives which are LSD1 inhibitors useful in the treatment of diseases such as cancer.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H252NO – PubChem

 

Brief introduction of (S)-Benzyl (4-(2,5-dioxooxazolidin-4-yl)butyl)carbamate

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Microstructure characterization and thermal analysis of hybrid block copolymer alpha-methoxy-poly(ethylene glycol)-block-poly[-(benzyloxycarbonyl)- l-lysine] for biomedical applications

Hybrid block copolymers, which combine the economy and processibility of synthetic polymers with the functionality and highly ordered structures of polypeptides, can enhance control over structure formation at the nanoscale, as well as afford interesting materials that interface with Nature for a diversity of biomedical applications, such as drug delivery, tissue engineering and bioimaging. Hybrid block copolymer, alpha-methoxy-poly(ethylene glycol)-b-poly[epsilon-(benzyloxycarbonyl)-l-lysine], MPEG-b-PLL(Z), was synthesized by anionic ring-opening polymerization in excellent yield, and fully characterized using IR, 1H, 13C and 2-D NMR, GPC, TGA, DTGA, DSC, MDSC and polarimetry. Its precursor NCA, epsilon-(benzyloxycarbonyl)- l-lysine N-carboxyanhydride, l-Lys(Z)-NCA, was prepared in 97% yield; and a double doublet observed in the 1850-1750 cm-1 absorption region of its infrared spectrum, for the characteristic NCA carbonyl absorption bands, is discussed.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2717NO – PubChem

 

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Synthetic Route of 102029-44-7, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.102029-44-7, Name is (R)-4-Benzyl-2-oxazolidinone, molecular formula is C10H11NO2. In a Article,once mentioned of 102029-44-7

Reverse Hydroxamate Inhibitors of Bone Morphogenetic Protein 1

Bone Morphogenetic Protein 1 (BMP1) inhibition is a potential method for treating fibrosis because BMP1, a member of the zinc metalloprotease family, is required to convert pro-collagen to collagen. A novel class of reverse hydroxamate BMP1 inhibitors was discovered, and cocrystal structures with BMP1 were obtained. The observed binding mode is unique in that the small molecule occupies the nonprime side of the metalloprotease pocket providing an opportunity to build in metalloprotease selectivity. Structure-guided modification of the initial hit led to the identification of an oral in vivo tool compound with selectivity over other metalloproteases. Due to irreversible inhibition of cytochrome P450 3A4 for this chemical class, the risk of potential drug-drug interactions was managed by optimizing the series for subcutaneous injection.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1873NO – PubChem

 

Brief introduction of 5-(Chloromethyl)oxazolidin-2-one

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Reference of 22625-57-6, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.22625-57-6, Name is 5-(Chloromethyl)oxazolidin-2-one, molecular formula is C4H6ClNO2. In a Patent,once mentioned of 22625-57-6

NON-FUSED TRICYCLIC COMPOUNDS

Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1415NO – PubChem