Category: 172900-69-5

Neelam, Uday Kumar published the artcileMetathesis approach to the formal synthesis of aliskiren, SDS of cas: 172900-69-5, the main research area is aliskiren Tekturna Rasilez renin inhibitor antihypertensive preparation enantioselective synthesis.

A formal synthesis of aliskiren by employing Grubbs second generation catalyst in a cross olefin metathesis, iron(III)-catalyzed vinylation and biocatalysis (enzyme catalysis) by using PLE is disclosed. The title compounds thus formed included (αS,γS,δS,ζS)-δ-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-γ-hydroxy-4-methoxy-3-(3-methoxypropoxy)-α,ζ-bis(1-methylethyl)benzeneoctanamide (Aliskiren) (I) and Aliskiren hemifumarate. The synthesis of the target compound was achieved by a convergent synthesis strategy. A reaction of (3S,5S)-5-[(1S,3S)-1-azido-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methylpentyl]dihydro-3-(1-methylethyl)-2(3H)-furanone with 3-amino-2,2-dimethylpropanamide gave an azide precursor for I, i.e., (αS,γS,δS,ζS)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-δ-azido-γ-hydroxy-4-methoxy-3-(3-methoxypropoxy)-α,ζ-bis(1-methylethyl)benzeneoctanamide.

Chemistry & Biology Interface published new progress about Amidation. 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, SDS of cas: 172900-69-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Fan published the artcileAn Improved and Economical Process for the Manufacture of the Key Intermediate of Aliskiren, a New Potent Renin Inhibitor, Computed Properties of 172900-69-5, the main research area is aliskiren intermediate preparation; aminomethoxymethoxypropoxybenzylmethylhexanoic acid preparation; lhexanoic acid aminomethoxymethoxypropoxybenzylmethyl preparation.

An improved, practical, economical and efficient process for the production of (2S,4S)-2-amino-4-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-methylhexanoic acid, a key intermediate of the new potent renin inhibitor of aliskiren, in a total yield over 30% is described. This process avoids expensive reagents and chromatog. purifications, and is easily scaled up in industry.

Organic Process Research & Development published new progress about aliskiren intermediate preparation; aminomethoxymethoxypropoxybenzylmethylhexanoic acid preparation; lhexanoic acid aminomethoxymethoxypropoxybenzylmethyl preparation. 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, Computed Properties of 172900-69-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Goeschke, Richard published the artcileThe nonchiral bislactim diethoxy ether as a highly stereo-inducing synthon for sterically hindered, γ-branched α-amino acids: A practical, large-scale route to an intermediate of the novel renin inhibitor aliskiren, Safety of 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, the main research area is gamma branched amino acid aliskiren intermediate preparation; stereoslective alkylation gamma branched amino acid preparation.

The diastereoselective synthesis of the sterically hindered, γ-branched α-amino acid derivative, I (R = CO2CMe3), and its N-[(tert-butoxy)carbonyl](Boc)-protected alc., both key intermediates of a novel class of nonpeptide renin inhibitors such as aliskiren, is described. Initially, the analogous Me ester was obtained by alkylation of the chiral Schoellkopf dihydropyrazine with a dialkoxy-substituted alkyl bromide, which proceeded with explicitly high diastereofacial selectivity (ds ≥98%) to give II, followed by mild acid hydrolysis and N-Boc protection. Conversely, the complete lack of stereocontrol and poor yields suggested, in addition to the anticipated shielding effect by the iPr group at C(2) of the auxiliary, steric repulsion between the MeO-C(6) and bulky residues in the proposed transition state, which would strongly disfavor both the Si and Re attack of the electrophile. Based on this rationale, alkylation of a readily accessible achiral diethoxy-dihydropyrazine was found to provide a 95:5 mixture of the product diastereoisomers in high yield, which afforded in two steps and after recrystallization enantiomerically pure I (R = CO2CMe3). Similarly, the stereochem. course for the alkylation reactions of the related alkyl bromides was investigated. The precursor bromides were efficiently synthesized via the diastereoselective alkylation of the Evans 3-isovaleroyloxazolidin-2-ones either with a bromide or with benzyl chloromethyl ether, and subsequent standard transformations. A practical and economical protocol of the preparation of I (R = CO2CMe3) on a multi-100-g scale is given. This is the first report of the application of an achiral dihydropyrazine, as a highly stereo-inducing synthon providing rapid access to a N-protected γ-branched α-amino acid with (2S) absolute configuration.

Helvetica Chimica Acta published new progress about Alkylation, stereoselective. 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, Safety of 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lindsay, Karl B. published the artcileFormal Total Synthesis of the Potent Renin Inhibitor Aliskiren: Application of a SmI2-Promoted Acyl-like Radical Coupling, Category: bromides-buliding-blocks, the main research area is renin inhibitor aliskiren total synthesis; samarium diiodide radical addition phenylalanine thioester acrylate.

A formal total synthesis of the potent renin inhibitor aliskiren is disclosed exploiting an alternative coupling strategy recently developed by the authors for the preparation of the hydroxyethylene isostere-based class of protease inhibitors. The 4-pyridyl thioester derivative of amino acid, CbzNHCH(CH2Ph)COS-Pyr (Pyr = 4-pyridyl), representing the C5-C9 fragment of the aliskiren carbon skeleton underwent a carbon chain extension via a SmI2-promoted radical addition to Bu acrylate. Introduction of the C3-iso-Pr group with the correct relative configuration was accomplished via stereoselective reduction of the obtained ketone with concomitant lactonization, followed by an aldol reaction with acetone. Further functional group and protecting group manipulation culminated in a formal total synthesis of aliskiren in 10 steps from the corresponding fully protected non-natural amino acid.

Journal of Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 172900-69-5 belongs to class bromides-buliding-blocks, name is 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, and the molecular formula is C17H27BrO3, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary