172900-71-9

Usage

Uses

Used in Pharmaceutical Industry:
Benzenepropanoic acid, 4-methoxy-3-(3-methoxypropoxy)-α-(1-methylethyl)-, (aR)is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into the molecular structures of drugs. Its unique functional groups facilitate the creation of new medicinal compounds with specific therapeutic properties.
Used in Organic Synthesis:
In the field of organic chemistry, Benzenepropanoic acid, 4-methoxy-3-(3-methoxypropoxy)-a-(1-methylethyl)-, (aR)- serves as a versatile building block for the synthesis of a wide range of organic compounds. Its presence of multiple functional groups allows for various chemical reactions, enabling the development of new materials and chemical entities with potential applications in different industries.
Used in Research Applications:
Benzenepropanoic acid, 4-methoxy-3-(3-methoxypropoxy)-α-(1-methylethyl)-, (aR)is also utilized in research settings to study the effects of structural variations on chemical and biological properties. Its unique stereochemistry, as indicated by the (aR)configuration, can provide insights into the role of stereoselectivity in chemical reactions and biological activities.
Used in Chemical Process Development:
Benzenepropanoic acid, 4-methoxy-3-(3-methoxypropoxy)-a-(1-methylethyl)-, (aR)-'s specific structural features make it valuable in the development of new chemical processes. It can be used to optimize reaction conditions, improve yields, and explore novel synthetic pathways, contributing to advancements in the chemical sciences.

Upstream product

• 387868-07-7 (E)-2-(4-methoxy-3-(3-methoxypropoxy)-benzylidene)-3-methylbutanoic acid 
• 621-59-0 isovanillin 
• 172900-75-3 4-methoxy-3-(3-methoxypropoxy)benzaldehyde 
• 173400-44-7 4(R)-benzyl-3-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propionyl}-oxazolidin-2-one 
• 172900-70-8 (R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol 
• 503-74-2 3-methylbutyric acid 
• 1350705-31-5 (R)-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one 
• 1350705-32-6 (4R)-3-(2S)-(2-(hydroxy(4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one 
• 1351987-18-2 butyl-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 325154-22-1 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid 
• 1381757-31-8 dimethyl-2(4-methoxy-3-(3-methoxypropyloxy)-benzyl)-2-isopropyl malonate 
• 109-19-3 butyl isovalerate 
• 1351987-19-3 C₂₁H₃₄O₆ 

Downstream Products

• 172900-70-8 (R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol 
• 172900-83-3 (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester 
• 878276-62-1 (2S,4S)-2-tert-butoxycarbonylamino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoic acid 
• 866030-36-6 [(1S,3S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester 
• 866030-38-8 Benzyl-{(1S,3S)-1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester 
• 866030-33-3 (2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine 
• 866030-35-5 tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate 
• 866030-37-7 Benzyl-[(1S,3S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-1-(methoxy-methyl-carbamoyl)-4-methyl-pentyl]-carbamic acid tert-butyl ester 
• 866030-40-2 ((1S,2R,4S)-2-Hydroxy-4-hydroxymethyl-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester 
• 866030-34-4 ((1S,2S,4S)-2-hydroxy-4-hydroxymethyl-1-((S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl)-5-methyl-hexyl)-carbamic acid tert-butyl ester 
• 172900-92-4 (1S,4S,2'S)-(4-benzyloxymethyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester 
• 173338-07-3 tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate 
• 866030-39-9 Benzyl-((1S,2R,4S)-4-benzyloxymethyl-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester 
• 173334-57-1 (2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide 

Relevant academic research and scientific papers

Synthesis of enantiopure (R)-2-(4-methoxy-3-(3-methoxypropoxy)-benzyl)-3-methylbutanoic acid-a key intermediate for the preparation of Aliskiren

The enantioselective hydrogenation of (E)-2-(4-methoxy-3-(3-methoxypropoxy)-benzylidene)-3-methylbutanoic acid (1) to (R)-2-(4-methoxy-3-(3-methoxypropoxy)-benzyl)-3-methylbutanoic acid (2)-a key intermediate in the synthesis of the pharmacologically important renin inhibitor Aliskiren-is described. The stereochemistry of the catalytic transformation has been studied using a number of homogeneous chiral Rh(I) and Ru(II) complexes bearing ferrocene-based phosphine ligands. The highest enantioselectivity for the homogeneous hydrogenation of 1 (up to 95% ee) was achieved with a [Rh(NBD)2]BF4 pre-catalyst (substrate/catalyst ratio 100:1, 10 bar H2, 40 °C, in MeOH). To bring the enantioselectivity to perfection an effective method for the isolation of the enantiopure carboxylic acid is suggested likewise.

A mixed-ligand approach enables the asymmetric hydrogenation of an α-isopropylcinnamic acid en route to the renin inhibitor aliskiren

An asymmetric hydrogenation process for the α-isopropyl dihydrocinnamic acid derivative 2, an intermediate for the renin inhibitor aliskiren (4), has been developed using a rhodium catalyst ligated with a chiral monodentate phosphoramidite and a nonchiral phosphine. Whereas catalysts based on two equivalents of monodentate phosphoramidites gave promising results, the rate of hydrogenation and ee of the product could be improved spectacularly by the addition of monodentate non-chiral triarylphosphines to these catalysts. This remarkable mixed-ligand catalyst has been identified using high-throughput experimentation. With the best catalysts turnover numbers >5000 mol mol -1, turnover frequencies >1000 mol mol-1 h -1, and ee's up to 95% have been achieved.

A aliskiren or its salt separation and analysis method

The invention relates to a separation analysis method using polysaccharide derivative-bonded and coated silica as a stationary phase and an organic solvent as a mobile phase for separation analysis of aliskiren and isomers thereof, effective separation of the aliskiren and isomers thereof can be realized, and the separation analysis method has the important meaning to the product quality control.

Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5-C6 Disconnection and CO2H-NH2 Equivalence

A novel synthesis of the renin inhibitor aliskiren based on an unprecedented disconnection between C5 and C6 was developed, in which the C5 carbon acts as a nucleophile and the amino group is introduced by a Curtius rearrangement, which follows a simultaneous stereocontrolled generation of the C4 and C5 stereogenic centers by an asymmetric hydrogenation. Operational simplicity, step economy, and a good overall yield makes this synthesis amenable to manufacture on scale.

Walphos versus biferrocene-based walphos analogues in the asymmetric hydrogenation of alkenes and ketones

Two representative Walphos analogues with an achiral 2,2″- biferrocenediyl backbone were synthesized. These diphosphine ligands were tested in the rhodium-catalyzed asymmetric hydrogenation of several alkenes and in the ruthenium-catalyzed hydrogenation of two ketones. The results were compared with those previously obtained on using biferrocene ligands with a C 2-symmetric 2,2″-biferrocenediyl backbone as well as with those obtained with Walphos ligands. The application of one newly synthesized ligand in the hydrogenation of 2-methylcinnamic acid gave (R)-2-methyl-3- phenylpropanoic acid with full conversion and with 92% ee. The same ligand was used to transform 2,4-pentanedione quantitatively and diastereoselectively into (S,S)-2,4-pentanediol with 98% ee.

NOVEL PROCESS FOR THE PREPARATION OF RENIN INHIBITORS

The present invention relates to an improved process for the preparation of compound of Formula-II, which is an intermediate in the preparation of Aliskiren and further conversion of compound of Formula-II into Aliskiren or its pharmaceutically acceptable salts. Formula-II wherein Ri and R2 are independently of one another H, Ci-C6 alkyl, C- C6 halogenalkyl, C]-C6 alkoxy, Ci-C6 alkoxy-Ci-C6 alkyl, or Ci-C6 alkoxy-Ci- C6 alkyloxy and X is halogen selected from fluoro, chloro, bromo and iodo

AN IMPROVED PROCESS FOR THE PREPARATION OF ALISKIREN

The present invention relates to an improved process for the preparation of renin inhibitor Aliskiren intermediates of Formula-II and further conversion into Aliskiren and its pharmaceutically acceptable salts.

An improved and economical process for the manufacture of the key intermediate of aliskiren, a new potent renin inhibitor

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 chromatographic purifications, and is easily scaled up in industry.

Biferrocene-based diphosphine ligands: Synthesis and application of walphos analogues in asymmetric hydrogenations

A total of four biferrocene-based Walphos-type ligands have been synthesized, structurally characterized, and tested in the rhodium-, ruthenium- and iridium-catalyzed hydrogenation of alkenes and ketones. Negishi coupling conditions allowed the biferrocene backbone of these diphosphine ligands to be built up diastereoselectively from the two nonidentical and nonracemic ferrocene fragments (R)-1-(N,N-dimethylamino)ethylferrocene and (SFc)-2- bromoiodoferrocene. The molecular structures of (SFc)-2- bromoiodoferrocene, the coupling product, two ligands, and the two complexes ([PdCl2(L)] and [RuCl(p-cymene)(L)]PF6) were determined by X-ray diffraction. The structural features of complexes and the catalysis results obtained with the newly synthesized biferrocene-based ligands were compared with those of the corresponding Walphos ligands.

ChenPhos: Highly modular P-stereogenic C1-symmetric diphosphine ligands for the efficient asymmetric hydrogenation of α-substituted cinnamic acids

These cats are purrfectionists: The ChenPhos ligands (see structure) showed dramatically higher catalytic activity in the title reaction than their C 2-symmetric predecessor with two dimethylaminoethyl-substituted ferrocenyl(phenyl)phosphanyl groups. The ready accessibility, extreme air stability, and high enantioselectivity, activity, and productivity of these ligands make them very promising for a wide range of practical applications. Copyright