Category: 138775-03-8

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Asymmetric Synthesis of Chiral Organofluorine Compounds: Use of Nonracemic Fluoroiodoacetic Acid as a Practical Electrophile and Its Application to the Synthesis of Monofluoro Hydroxyethylene Dipeptide Isosteres within a Novel Series of HIV Protease Inhibitors, published in 2001-08-01, which mentions a compound: 138775-03-8, Name is (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, Molecular C18H24N2O6, Formula: C18H24N2O6.

Two stereoselective routes to a series of diastereomeric inhibitors of HIV protease, monofluorinated analogs of the Merck HIV protease inhibitor indinavir, are described. The two routes feature stereoselective construction of the fluorinated core subunits by asym. alkylation reactions. The first-generation syntheses were based on the conjugate addition of the lithium enolate derived from pseudoephedrine α-fluoroacetamide to trans-nitroalkene Ph-CH2-CH:CH-NO2, a modestly diastereoselective transformation. A more practical second-generation synthetic route was developed that is based on a novel method for the asym. synthesis of organofluorine compounds, by enolate alkylation using optically active fluoroiodoacetic acid as the electrophile in combination with a chiral amide enolate. Resolution of fluoroiodoacetic acid with ephedrine provides either enantiomeric form of the electrophile in ≥96% ee. Alkylation reactions with this stable and storable chiral fluorinated precursor are shown to proceed in a highly stereospecific manner. With the development of substrate-controlled syn- or anti-selective reductions of α-fluoro ketones (I; F, CH2Ph trans and I; F, CH2Ph = cis; diastereomeric ratios 12:1-84:1), efficient and stereoselective routes to each of the four targeted inhibitors were achieved. The optimized synthetic route to the most potent inhibitor (II; Ki = 2.0 nM) proceeded in seven steps (87% average yield per step) from aminoindanol hydrocinnamide and (S)-fluoroiodoacetic acid, and allowed for the preparation of more than 1 g of this compound The inhibition of HIV-1 protease by each of the fluorinated inhibitors was evaluated in vitro, and the variation of potency as a function of inhibitor stereochem. is discussed.

After consulting a lot of data, we found that this compound(138775-03-8)Formula: C18H24N2O6 can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid( cas:138775-03-8 ) is researched.Formula: C18H24N2O6.Ibrahim, Mohamed A.; Johnson, Henry W. B.; Jeong, Joon Won; Lewis, Gary L.; Shi, Xian; Noguchi, Robin T.; Williams, Matthew; Leahy, James W.; Nuss, John M.; Woolfrey, John; Banica, Monica; Bentzien, Frauke; Chou, Yu-Chien; Gibson, Anna; Heald, Nathan; Lamb, Peter; Mattheakis, Larry; Matthews, David; Shipway, Aaron; Wu, Xiang; Zhang, WenTao; Zhou, Sihong; Shankar, Geetha published the article 《Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists》 about this compound( cas:138775-03-8 ) in Journal of Medicinal Chemistry. Keywords: amide preparation sphingosine phosphate receptor antagonistic pharmacokinetics. Let’s learn more about this compound (cas:138775-03-8).

A series of subtype selective sphingosine 1-phosphate receptor 1 (S1P1) antagonists are disclosed. Our high-throughput screening campaign revealed hit I for which an increase in potency and mouse oral exposure was achieved with minor modifications to the chem. scaffold. In vivo efficacy revealed that at high doses compounds II(X = F, Cl) inhibited tumor growth. Further optimization of our lead series led to the discovery of proline derivatives III(R = 1,2,3-triazol-1yl) (XL541) and III(R = 1,2,3-triazol-2yl) which had similar efficacy as our first generation analogs at significantly lower doses. Analog III(R = 1,2,3-triazol-1yl) displayed excellent pharmacokinetics and oral exposure in multiple species.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists, published in 2012-02-09, which mentions a compound: 138775-03-8, mainly applied to amide preparation sphingosine phosphate receptor antagonistic pharmacokinetics, Recommanded Product: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid.

A series of subtype selective sphingosine 1-phosphate receptor 1 (S1P1) antagonists are disclosed. Our high-throughput screening campaign revealed hit I for which an increase in potency and mouse oral exposure was achieved with minor modifications to the chem. scaffold. In vivo efficacy revealed that at high doses compounds II(X = F, Cl) inhibited tumor growth. Further optimization of our lead series led to the discovery of proline derivatives III(R = 1,2,3-triazol-1yl) (XL541) and III(R = 1,2,3-triazol-2yl) which had similar efficacy as our first generation analogs at significantly lower doses. Analog III(R = 1,2,3-triazol-1yl) displayed excellent pharmacokinetics and oral exposure in multiple species.

After consulting a lot of data, we found that this compound(138775-03-8)Recommanded Product: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid(SMILESS: O=C(N1[C@H](C(O)=O)CN(C(OCC2=CC=CC=C2)=O)CC1)OC(C)(C)C,cas:138775-03-8) is researched.COA of Formula: C3H7ClO2. The article 《Synthesis of Enantiopure Piperazines via Asymmetric Lithiation-Trapping of N-Boc Piperazines: Unexpected Role of the Electrophile and Distal N-Substituent》 in relation to this compound, is published in Journal of the American Chemical Society. Let’s take a look at the latest research on this compound (cas:138775-03-8).

A new method for the synthesis of enantiopure α-substituted piperazines via direct functionalization of the intact piperazine ring is described. The approach utilizes the asym. lithiation-substitution of an α-methylbenzyl-functionalized N-Boc piperazine using s-BuLi/(-)-sparteine or (+)-sparteine surrogate and provides access to a range of piperazines (as single stereoisomers). Optimization of the new methodol. required a detailed mechanistic study. Surprisingly, it was found that the main culprits affecting the yield and enantioselectivity were the electrophile (the last reagent to be added to the reaction flask) and the distal N-substituent. The mechanistic studies included optimization of lithiation times using in situ IR spectroscopy, identification of a ring-fragmentation of the lithiated piperazines (that could be minimized with sterically hindered N-alkyl groups), and use of a novel “”diamine switch”” strategy to improve enantioselectivity with certain electrophiles. The methodol. was showcased with the preparation of an intermediate for Indinavir synthesis and the stereoselective synthesis of 2,5-trans- and 2,6-trans-piperazines.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Recommanded Product: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, is researched, Molecular C18H24N2O6, CAS is 138775-03-8, about Synthesis of N,N’-Orthogonally Protected (S)-Piperazine-2-carboxylic Acid. Author is Warshawsky, Alan M.; Patel, Meena V.; Chen, Teng-Man.

(S)-1-tert-butoxycarbonyl-4-benzyloxycarbonyl-2-piperazinecarboxylic acid was prepared in 4 steps and 40% overall yield from N-tert-butoxycarbonyl-L-serine β-lactone. The sequence required only a single chromatog. purification and yielded optically pure product.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of C18H24N2O6. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, is researched, Molecular C18H24N2O6, CAS is 138775-03-8, about Synthesis of N,N’-Orthogonally Protected (S)-Piperazine-2-carboxylic Acid. Author is Warshawsky, Alan M.; Patel, Meena V.; Chen, Teng-Man.

(S)-1-tert-butoxycarbonyl-4-benzyloxycarbonyl-2-piperazinecarboxylic acid was prepared in 4 steps and 40% overall yield from N-tert-butoxycarbonyl-L-serine β-lactone. The sequence required only a single chromatog. purification and yielded optically pure product.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, is researched, Molecular C18H24N2O6, CAS is 138775-03-8, about Discovery of (2S)-N-[(1R)-2-[4-cyclohexyl-4-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperidinyl]-1-[(4-fluorophenyl)methyl]-2-oxoethyl]-4-methyl-2-piperazinecarboxamide (MB243), a potent and selective melanocortin subtype-4 receptor agonist.

We report the discovery and optimization of substituted 2-piperazinecarboxamides as potent and selective agonists of the melanocortin subtype-4 receptor. Further in vivo development of lead agonist, MB243, is disclosed.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Discovery of (2S)-N-[(1R)-2-[4-cyclohexyl-4-[[(1,1-dimethylethyl)amino]carbonyl]-1-piperidinyl]-1-[(4-fluorophenyl)methyl]-2-oxoethyl]-4-methyl-2-piperazinecarboxamide (MB243), a potent and selective melanocortin subtype-4 receptor agonist, published in 2005-01-03, which mentions a compound: 138775-03-8, Name is (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, Molecular C18H24N2O6, Application of 138775-03-8.

We report the discovery and optimization of substituted 2-piperazinecarboxamides as potent and selective agonists of the melanocortin subtype-4 receptor. Further in vivo development of lead agonist, MB243, is disclosed.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application In Synthesis of (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid, is researched, Molecular C18H24N2O6, CAS is 138775-03-8, about Synthesis of Enantiopure Piperazines via Asymmetric Lithiation-Trapping of N-Boc Piperazines: Unexpected Role of the Electrophile and Distal N-Substituent. Author is Firth, James D.; O’Brien, Peter; Ferris, Leigh.

A new method for the synthesis of enantiopure α-substituted piperazines via direct functionalization of the intact piperazine ring is described. The approach utilizes the asym. lithiation-substitution of an α-methylbenzyl-functionalized N-Boc piperazine using s-BuLi/(-)-sparteine or (+)-sparteine surrogate and provides access to a range of piperazines (as single stereoisomers). Optimization of the new methodol. required a detailed mechanistic study. Surprisingly, it was found that the main culprits affecting the yield and enantioselectivity were the electrophile (the last reagent to be added to the reaction flask) and the distal N-substituent. The mechanistic studies included optimization of lithiation times using in situ IR spectroscopy, identification of a ring-fragmentation of the lithiated piperazines (that could be minimized with sterically hindered N-alkyl groups), and use of a novel “”diamine switch”” strategy to improve enantioselectivity with certain electrophiles. The methodol. was showcased with the preparation of an intermediate for Indinavir synthesis and the stereoselective synthesis of 2,5-trans- and 2,6-trans-piperazines.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Myers, Andrew G.; Barbay, Joseph K.; Zhong, Boyu published the article 《Asymmetric Synthesis of Chiral Organofluorine Compounds: Use of Nonracemic Fluoroiodoacetic Acid as a Practical Electrophile and Its Application to the Synthesis of Monofluoro Hydroxyethylene Dipeptide Isosteres within a Novel Series of HIV Protease Inhibitors》. Keywords: fluoroacetamide nitroalkene diastereoselective conjugate addition preparation HIV1 protease inhibitor; asym alkylation fluoroiodoacetate amide enolate preparation HIV1 protease inhibitor; fluoro ketone preparation HIV1 protease inhibitor.They researched the compound: (S)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid( cas:138775-03-8 ).Category: iodides-buliding-blocks. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:138775-03-8) here.

Two stereoselective routes to a series of diastereomeric inhibitors of HIV protease, monofluorinated analogs of the Merck HIV protease inhibitor indinavir, are described. The two routes feature stereoselective construction of the fluorinated core subunits by asym. alkylation reactions. The first-generation syntheses were based on the conjugate addition of the lithium enolate derived from pseudoephedrine α-fluoroacetamide to trans-nitroalkene Ph-CH2-CH:CH-NO2, a modestly diastereoselective transformation. A more practical second-generation synthetic route was developed that is based on a novel method for the asym. synthesis of organofluorine compounds, by enolate alkylation using optically active fluoroiodoacetic acid as the electrophile in combination with a chiral amide enolate. Resolution of fluoroiodoacetic acid with ephedrine provides either enantiomeric form of the electrophile in ≥96% ee. Alkylation reactions with this stable and storable chiral fluorinated precursor are shown to proceed in a highly stereospecific manner. With the development of substrate-controlled syn- or anti-selective reductions of α-fluoro ketones (I; F, CH2Ph trans and I; F, CH2Ph = cis; diastereomeric ratios 12:1-84:1), efficient and stereoselective routes to each of the four targeted inhibitors were achieved. The optimized synthetic route to the most potent inhibitor (II; Ki = 2.0 nM) proceeded in seven steps (87% average yield per step) from aminoindanol hydrocinnamide and (S)-fluoroiodoacetic acid, and allowed for the preparation of more than 1 g of this compound The inhibition of HIV-1 protease by each of the fluorinated inhibitors was evaluated in vitro, and the variation of potency as a function of inhibitor stereochem. is discussed.

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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com