By Michael Smith
This paintings offers a accomplished assessment of, and the commonest and beneficial equipment for, the synthesis of non-alpha-amino acids, relatively amino acids which are key man made intermediates or vital compounds of their personal correct. awareness is paid to acyclic amino acids C3-C10 together with amino alkanoic carboxylic acids, aminoalkenoic acids and aminoalkynoic acids.
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109. 109 reduction) for converting a key intermediateto an amine, when compared to previous examples in this section. The traditional reagent for dissolving metal reductions is sodium metal in liquid ammonia. 110. 110 Na . 111 Just as aldehydes and ketonesreact with hydroxylamine to form an oxime, they react with hydrazine derivativesto give hydrazones. The C=N moiety in these hydrazones can be reduced to give amines. 112 was obtained. Reduction of the C=N moiety used a reagent newto this section.
Miscellaneous Amino Acids There are. of course, many aminoacids that canbe used to prepare new amino acids. 23Z,),which reacted with nitrous acid (HONO, generated in situ by reaction with sodiumnitrite and acid) to convert one aminogroup to an alcohol moiety. 137 Protection of nitrogen andesterification with diazomethane was followed by an Amdt-Eistert13* reaction to give the 3-aminoderivative. 235). 2. ClCqEt ,NMN 4. PhCOzAg 5. HC1 (62%) . 236) converted to a nitrile via dehydration ofthe amidemoiety.
Conc. 160 Nitriles can be used in reactions other than displacement. The Boc-protected aldehyde derived from alanine(known as N-Boc alinal. 161) was condensed with potassium cyanide togive a cyanohydrin. 95 1. NaHSO? BocHN 1C H 0% 3. HCl 4. 161 Specialized variations are also possible. 163 with methanol, however, gave methyl3-amino-2-cyano-3-methoxyprop-2-enoate. 163 aq. ii. Carboxyl Surrogates (CarbonDioxide) A different approach uses the reaction of an organometallic with theelectrophilic carbonyl of carbon dioxide, giving a carboxyl group directly.