5- pentanoic acid amide

In the case of monolayers of the compound A-tetradecyl-y, 5-dihydroxy-pentanoic acid amide (TDHPAA), chiral discrimination effects in the domain structures were observed by BAM. The small, spear-like crystals showed a longer and shorter branch at one end and were seen to be mirror images of each other when the two enantiomers were compared. The racemic mixture formed a symmetric, almost straight and narrow crystallite for its condensed phase. 

Benzyl cyanide is first reacted with 2-butylbromide in the presence of sodium amide to give 2-phenyl-3-methylvaleronitrile which is hydrolyzed by sulfuric acid to give 3-methyl-2-phenyl-pentanoic acid. 24 g of 2-phenyl-3-methyl-pentanoic acid are heated for one hour at 175° to 185°C with 30 g of 2-diethylaminoethanol and 0.5 g of sodium methylate. The excess diethyl-aminoethanol is removed in vacuo, the residue is dissolved in 300 cc of 2 N-acetic acid, the acid solution is shaken with ether and made alkaline with concentrated potassium carbonate solution and ice. The ether solution Is washed with water, dried with sodium sulfate and evaporated. The residue is distilled under high vacuum, yielding 20 to 21 g of the basic ester (60% of the theoretical) is obtained, the ester boiling at 98° to 100°C at a pressure of 0.03 mm. The hydrochloride of the ester melts at 112° to 113°C and the methobromide at 100° to 101°C. 

Song, Y., Bowersox S.S., Connor, D.T., Dooley D.J., Lotarski S.M., Malone Th., Miljanich G., Millerman E., Rafferty M.F., Rock D., Roth B. D., Schmidt, J., Stoehr, S., Szoke, B. G., Taylor, Ch., Vartanian, M., Wang, Y.-X. (S)-4-Methyl-2-(methylamino)pentanoic acid [4,4-bis(4-fluorophenyl)-butyl]amide hydrochloride, a novel calcium channel antagonist, Is efficacious in several animal models of pain, J. Med. Chem. 2000, 43, 3474-3477. 

Valproyltaurinamide derivatives, (II), prepared by amidation of 2-propyl-pentanoic acid (valproic acid) using 2-aminoethanesulfonic acid (taurine) previously prepared by the authors (2) was effective as an antiseizure medicament. 

The suffixes -oic acid, -oyl halide, -amide, -nitrile, and -al are used when the functional group is at the end of a carbon chain, as in pentanoic acid. The endings -carboxylic acid, etc., are used when the group is attached to a ring, as in 2-pyridinecarboxylic acid. 

The acid-catalyzed hydrolysis of butanamide proceeds as expected to give butanoic acid, 7. An example is the acid-catalyzed hydrolysis of the tertiary amide iV,iV-diethyl-3-phenylpentanamide (34) to give 3-phenylpentanoic acid (35). The initial product is iV,AT-diethylamine, but under the acid-catalyzed conditions, the basic amine reacts to form the observed product, ammonium salt, 36. Secondary and primary amides react in an identical manner the leaving group is an amine for the secondary amide, but it is ammonia for the primary amide. Acid hydrolysis of pentanamide, for example, gives pentanoic acid and ammonia (NHg) and, under acid conditions, the ammonia is converted to the ammonium ion (NH4+). When amides are heated with aqueous hydroxide, the products are the salt of the carboxylic acid and the amine. Acid hydrolysis of the carboxylate salt generates the acid, as with saponification. 

A similar "oxime-driven" methodology was applied to the aldehyde moiety in 4,4-dimethyl-glutaraldehyde 1.100), which was converted to oxime I.IOI. In this example, catalytic hydrogenation of the oxime gave an amine, but the amino acid spontaneously cyclized to give 4,4-dimethyl valerolactam, 1.102 (see chapter two, section 2.3). An acid hydrolysis step was required to liberate 5-araino-4,4-dimethyl-pentanoic acid, 1.103. In some cases, reduction in this type of system leads to a mono-amide as an intermediate product rather than a lactam. Similar formation of... 

Na-bis(trimethylsilyl)amide in abs. tetrahydrofuran added at -10 to 0° with stirring to trimethylsilyl N,N-bis(trimethylsilyl)glycinate in the same solvent under dry Ng (maintained throughout the reaction), allowed to stand a short while, then a soln. of l-(3-bromopropyl)thymine (prepn. s. 395) in abs. tetrahydrofuran added dropwise, stirred 2 days at 40°, filtered, dissolved in water, acidified with dil. HCl to pH 5-6, and coned, slowly 2-amino-5-(thymin-l-yl)pentanoic acid. Y 64%. F. e. s. F.-S. Tjoeng et al., B. 109, 2615 (1976). 

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