170282-44-7

Upstream product

• 7664-93-9 sulfuric acid 
• 6939-36-2 4-(2-methylphenyl)-4-oxobutanoic acid 
• 144-55-8 sodium hydrogencarbonate 
• 1663-39-4 tert-Butyl acrylate 
• 932-31-0 ortho-tolylmagnesium bromide 
• 75-65-0 tert-butyl alcohol 
• 33872-80-9 o-tolyl magnesium chloride 
• 115-11-7 isobutene 

Downstream Products

• 170282-45-8 tert-butyl (R)-4-hydroxy-4-(2-methylphenyl)butanoate 
• 170282-46-9 tert-butyl (S)-4-hydroxy-4-(2-methylphenyl)butanoate 

Relevant academic research and scientific papers

Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones

Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.

Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters

The first general asymmetric synthesis of γ,γ-disubstituted γ-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched γ-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98 %.

Substituted phenyl compounds

Compounds of formula (I) are described wherein R1is hydrogen, -(lower alkyl)q(CO2R6or OH), —CN, —C(R7)═NOR8, NO2, —O(lower alkyl)R9, —C≡C—R10, —CR11═C(R12)(R13), —C(═O)CH2C(═O)CO2H, —CO(R14), alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, thiocarbamoyl, substituted carbamoyl, substituted thiocarbamoyl, sulphamoyl or an optionally substituted nitrogen-containing ring, m, n, o and p are independently zero or 1 and R2, R3, R4and R5are various groups; and physiologically acceptable salts, N-oxides and prodrugs thereof. The compounds have endothelin antagonist activity and are useful as pharmaceuticals.

Selective endothelin a receptor antagonists. 3. Discovery and structure- activity relationships of a series of 4-phenoxybutanoic acid derivatives

The third in this series of papers describes our further progress into the discovery of a potent and selective endothelin A (ET(A)) receptor antagonist for the potential treatment of diseases in which a pathophysiological role for endothelin has been implicated. These include hypertension, ischemic diseases, and atherosclerosis. In earlier publications we have outlined the discovery and structure-activity relations of two moderately potent series of nonpeptide ET(A) receptor antagonists. In this paper, we describe how a pharmacophore model for ET(A) receptor binding was developed which enabled these two series of compounds to be merged into a single class of 4-phenoxybutanoic acid derivatives. The subsequent optimization of in vitro activity against the ET(A) receptor led to the discovery of (R)-4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(2- methylphenyl)butanoic acid (12m). This compound exhibits low-nanomolar binding to the ET(A) receptor and a greater than 1000-fold selectivity over the ET(B) receptor. Data are presented to demonstrate that 12m is orally bioavailable in the rat and is a functional antagonist in vitro and in vivo of ET-1-induced vasoconstriction.