52144-91-9Relevant articles and documents
A facile preparation of α-aryl carboxylic acid via one-flow arndt-eistert synthesis
Fuse, Shinichiro,Otake, Yuma,Mifune, Yuto,Tanaka, Hiroshi
, p. 1657 - 1661 (2015/11/10)
An efficient, one-flow Arndt-Eistert synthesis was demonstrated. A sequence of acid chloride formation-nucleophilic acyl substitution-Wolff rearrangement-nucleophilic addition was performed in a microflow system without isolating any intermediates, which
A urinary metabolite of Δ1-tetrahydrocannabinol. The first synthesis of 4''-hydroxy-Δ1-tetrahydrocannabinol-7-oic acid labelled with deuterium
Szirmai,Odqvist,Halldin
, p. 309 - 324 (2007/10/03)
The first synthesis of 4''-hydroxy-Δ1-THC-7-oic acid, one of the three major metabolites of Δ1-THC identified in human urine is discussed. Methyl 4-(3,5-dihydroxyphenyl)butanoate (8) was prepared from 3,5-dihydroxybenzoic acid in an overall yield of 15%. 8 was condensed with a terpene synthon (9) under acidic conditions followed by hydrolysis and conversion of the 4''-carboxylic acid function to the corresponding methyl ketone using methyllithium. Reduction with NaBH4 afforded the secondary alcohol in the side-chain. Acetylation and removal of the 1,3-dithiane masking group gave the aldehyde in C-7-position which was further oxidized using NaClO2 followed by deacetylation to give the desired metabolite 14. The same procedure may be used for the synthesis of unlabelled 4''-hydroxy-Δ1-THC-7-oic acid.
Orally active bronchospasmolytic compounds and their preparation
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, (2008/06/13)
Novel compounds are disclosed having useful activity as bronchodilators of improved longevity of action and reduced incidence of side effects. These compounds are described by the formula: EQU1 wherein R1 is a member of the class consisting of tertiary butyl and cyclobutyl, and R2 is a hydrogen or 2 to 5 carbon atom acyl radical, and pharmaceutically acceptable salts thereof. The activity of these compounds is compared to previously known bronchodilators such as 1-(3', 5'-dihydroxyphenyl)-2-(isopropylamino)-ethanol, having the common name orciprenaline, and 1-(3', 4'-dihydroxyphenyl-2-isoproplyamino-ethanol, having the common name isoprenaline.