4-Methylhexanoic acid

A similar problem was noted by researchers from Pfizer and Dowpharma in their synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin, 5) via the enantioselective hydrogenation of an acrylonitrile-type substrate 3 (Scheme 44.6) [41]. 

Biological. Riser-Roberts (1992) reported 2- and 5-methylhexanoic acids as metabolites by the microorganism Pseudomonas aeruginosa. 

Methylhexanoic acid, see 5-Methylhexane Methyl hydrogen phthalate, see Dimethyl phthalate Methyl hydroperoxide, see 1,1-Dimethylhydrazine Methylhydroquinone, see 2-Methylphenol... 

Recently, Hu and co-workers, at Pfizer, filed a patent application on a process to prepare pregabalin (2) via enzymatic resolution (Hu et al., 2005). The Pfizer researchers investigated a large number of commercially available hydrolases to catalyze the hydrolysis of (3-cyanodiester 59, an intermediate from the malonate route (Scheme 16.16), to form (35)-3-cyano-2-ethoxcarbonyl-5-methylhexanoic acid potassium salt (71)... 

The aliphatic acids isolated from a California crude petroleum by Lochte and coworkers (31) include 2-methylpentanoic acid, 3-methylpentanoic acid, n-hexanoic acid, 2-methylhexanoic acid, 3-methylhexanoic acid, 4-methylhexanoic acid, 5-methylhexanoic acid, n-heptanoic acid, n-octanoic acid, and n-nonanoic acid. 

Several carboxylic acid derivatives that might be accessible using biocatalysis were used as precursors for the synthesis of pregabaiin and could potentially be prepared using biocatalysis (Scheme 8.4). Among these, 2-carboxyethyl-3-cyano-5-methylhexanoic acid (13) and 3-cyano-5-methylhexanoic acid (5) appeared as the... 

Sylvatine (C24H3303N mp 112° [a]D +0°) isolated from this plant was shown to be an amide of piperic acid. Mass and other spectra indicated structure 148 and confirmation was achieved by reduction, hydrolysis, and/or oxidation, the product of the latter process being 5-methylhexanoic acid (136). 

Amino- 5-methylhexanoic acid 2-Amino-2,3-dimethyl-pentanoic acid 2-Amino-2,4-dimethyl-pentanoic acid 2-Amino-3,4-dimethyl-pentanoic acid... 

Introduction of an isopropyl group a to the carboxyl group of a 5-methylhexanoic acid derivative would lead to the lavandulyl skeleton. This has been carried out by making the lithium enolate (230) of methyl 5-methyl-2-hexenoate. After treatment with acetone and reduction of the ester group to a primary alcohol, the diol 231 was obtained. ... 

LeuMstin [(2/(,35)-3-amino-2-hydroxy-2-(IA/-imida-zol-4-ylmethyl)-5-methylhexanoic acid]. 

Preparative scale electrolysis gave different products depending on whether the electrolyte was quenched immediately after the electrolysis or not. In the first case the major products of heptanoic acid, 4-methylpentanoic acid, 5-methylhexanoic acid or octanoic acid were always y- to -lactones with overall yields of 40-70% (equation 17a). After being some time in the acidic electrolyte the lactones are converted to a,j8-unsaturated ketones by a chemical follow-up reaction (equation 17b). 

Using your roadmaps as a guide, show how to convert 4-methyl-l-pentene and carbon dioxide into 5-methylhexanoic acid. You must use 4-methyl-l-pentene and carbon dioxide as the source of all carbon atoms in the target molecule. Show all reagents and aU molecules s)mthesized along the way. 

A different study generated the lithium imine of 2.118 and condensed it with ester 2.119 to give 2.120. Deprotection of the lactam nitrogen with ceric ammonium nitrate and acid hydrolysis led to formation of 3-amino-2-hydroxy-5-methylhexanoic acid, 2.727.57... 

In addition to the all-aromatic AB polymers, which are infusible and generally insoluble (6), several polymers which contain alkyl chains have been obtained. The earliest such benzoxazole polymers were prepared from the 0)-(3-amino-4-hydroxypheny1-derivatives of propionic acid, 3-methyl-butyric acid and 5-methylhexanoic acid (7). Thermal polymerization of the propionic acid monomer under nitrogen atmosphere with gradual temperature increase from 195 to 285o gave a polymer which was... 

Pregabalin [Lyrica (S)-3-(aminomethyl)-5-methylhexanoic acid] is an unnatural amino acid that is effective in the treatment of chronic pain. 

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