Glycinal, reaction with

Carbodi-imide-mediated reaction with epichlorohydrin-activated agarose previously treated with glycine Reaction with a syw-trichlorotriazine-activated polystyrene anion exchanger reaction with 1,4-benzoqumone-activated aminopropyl silica reaction with an N-hydroxysuccinimide ester derivative of 3-succinimidopropyl silica Carbodi-imide- or 2,4-toluenedi-isocyanate-mediated reaction with amino-or carboxy-aerosU... 

Chloroacetic acid can be esterified and aminated to provide useful chemical intermediates. Amphoteric agents suitable as shampoos have been synthesized by reaction of sodium chloroacetate with fatty amines (4,5). Reactions with amines (6) such as ammonia, methylamine, and trimethylamine yield glycine [66-40-6J, sarcosine [107-97-17, and carhoxymethyltrimethylammonium chloride, respectively. Reaction with aniline forms /V-phenylglycine [103-01 -5] a starting point for the synthesis of indigo (7). 

This carboxyborane can undergo an amine exchange reaction with Hquid ammonia (eq. 7) to yield the boron analogue of glycine, the simplest alpha-amino acid (13). There has been a great deal of work on the pharmacological activity of these amino acid analogues (14). 

The derivative of glycine, prepared from benzophenone (cat. BF3 Et20, xylene, reflux, 82% yield), has found considerable use in the preparation of amino acids. It can also be prepared by an exchange reaction with benzophenoneimine (Ph2C=NH, CH2CI2, rt). ... 

In a more recent work the same research group has applied cyclic and acyclic vinyl ethers in the oxazaborolidinone-catalyzed 1,3-dipolar cycloaddition reaction with nitrones [30]. The reaction between nitrone 5 and 2,3-dihydrofuran 6 with 20 mol% of the phenyl glycine-derived catalyst 3c, gave the product 7 in 56% yield as the sole diastereomer, however, with a low ee of 38% (Scheme 6.9). 

Acetic anhydride, condensation with and acetylation of glycine, 46, 1 in cyclization of c-formylphenoxy-acetic acid to coumarone, 46, 28 in cyclization of hippuric acid to 2-phenyl-5-oxazolone, 47, 101 reaction with N-nitroso-N-phenyl-glycine to yield 3-phenylsydnone, 46,96... 

The relative configuration of the diastcrcomers obtained on reaction of A-benzoyl a-methoxy-glycine methyl ester and various activated cyclohexenes is dependent on the cyclohexene substituent88. Whereas the boron trifiuoride catalyzed reaction with l-(4-morpholinyl)cyclohexene gives predominantly the awt/ -isomer, the. vrn-isomcr is predominantly formed in the titan-ium(IV) chloride catalyzed reaction with trimethylsilyloxycyclohexene. These results arc explained by a cyclic and an acyclic transition state, respectively. As expected, acetoxycyclohex-ene is less reactive. 

In a less straightforward way, D-glucose (393) underwent a Maillard-type reaction with an excess of glycine (394) under microwave irradiation to afford 5-hydroxy-l,3-dimethyl-2(l/f)-quinoxahnone (395) as a major product, Repetition with labeled reactants suggested that the product contained six carbon atoms from the sugar and four from the amino acid on this evidence, a detailed mechanism has been postulated. 

In contrast, when excess amounts of the HHTs derived from simple aliphatic glycinate esters, such as 25, were used in excess in reactions with diaryl phosphites (SO), the related glyphosate aminals containing aryl phosphonate esters 46 were isolated in low yield (5-15%). Like many aminals, these triesters 46 were acid-sensitive and were quantitatively converted to the corresponding triester strong acid salts 47 upon treatment with either HCl or methanesulf onic acid (27). 

Ethonam (99), an imidazole derivative with a very different substitution pattern, is also reported to possess antifungal activity. To prepare it, alkylation of aminotetralin 94 with methylchloro-acetate gives the glycine derivative 95. Heating with formic acid then affords the amide 96 this compound is then reacted with ethyl formate to yield hydroxymethylene ester 97. Reaction with isothio-cyanic acid gives the imidazole-2-thiol 98. (The... 

The range of complexes which can be formed by just one amino-acid, glycine, and one Pt(II) complex, PtCll-, will now be illustrated (45, 46). Direct reaction with glycine gives the bis-(cis)-glycinato Pt(II) complex... 

Alanine, valine, and leucine, (amino-acids with alkyl substituents only) react in a manner very like that of glycine (49—53). All the reactions are rather slow and boiling solutions are normally employed in the preparative reactions. With the cis- and /raws-isomers of Pt(NHs)2Cl2 substitution of the chloride only occurs. Since the tfraws-labilising influence of the incoming groups of the amino-acids is very small, the —NH2 groups remain stable. Consequently chelated complexes are only formed by the amino-acids in the case of the cts-isomer. 

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