Chloride phenylglycine

On acetylation it gives acetanilide. Nitrated with some decomposition to a mixture of 2-and 4-nitroanilines. It is basic and gives water-soluble salts with mineral acids. Heating aniline sulphate at 190 C gives sulphanilic add. When heated with alkyl chlorides or aliphatic alcohols mono- and di-alkyl derivatives are obtained, e.g. dimethylaniline. Treatment with trichloroethylene gives phenylglycine. With glycerol and sulphuric acid (Skraup s reaction) quinoline is obtained, while quinaldine can be prepared by the reaction between aniline, paraldehyde and hydrochloric acid. 

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). 

Chlorophenylacetic acid has been prepared from mandeloni-trile and hydrochloric acid in a sealed tube, from mandelic acid and hydrochloric acid in a sealed tube/ from a-nitrostyrene and hydrochloric acid in a sealed tube, from phenylglycine, hydrochloric acid, and sodium nitrite, from mandelic acid and phosphorus pentachloride (to give the acid chloride which is then hydrolyzed), and, in poor yield, from mandelic acid and thionyl chloride. In the method described, ethyl mandelate is prepared according to Fischer and Speier. The conversion to the chloroester and the acid hydrolysis step are modifications of a preparation described by McKenzie and Barrow. ... 

N-Nitroso N phenylglycine, 46, 96 reaction with acetic anhydride to yield 3 phenylsydnone, 46, 96 Nitrosyl chloride, addition to bicyclo-[2 2 ljhepta 2,5 diene, 46, 75 2,4-Nonanedione, 47, 92 Nonane, 1,1,3 trichloro-, 46,104 Nortricyclanol, 46, 74 oxidation by chromic acid, 46, 78 Nortricyclanone, 46, 77 Nortncj clyl acetate 46, 74 frombicyclo[2 2 ljhepta 2,5 dieneand acetic acid, 46, 74 saponification of, 46, 75... 

This procedure is a modification of preparations of 3-phen)d, sydnone described earlier. The dehydration of N-nitroso-N phenylglycine has also been effected by the use of thionyl chloride and pyridine in dioxane, thionyl chloride in ethertrifluoroacetic anhydride in etherand diisopropylcarbodiimide in water or by reaction of the alkali metal salts of N-nitroso-N-phenylglycine with phosgene or benzenesulfonyl chloride in water or with acetyl chloride in benzene. ... 

A method of directly acylating 6-APA with phenylglycine chloride hydrochloride also has been proposed [37]. 

Acylation of 6-APA with an amino acid leads to a compound that bears some resemblance to a dipeptide. The coupling product with D-phenylglycine shows an enhanced antibacterial spectmm, possibly as a result of a better fit to the cell wall cross-hnking enzyme. The compound also shows improved oral absorption. One synthesis starts with the acylation of 6-APA with the acid chloride (3-3) from D-2-azidophenylacetic acid. Catalytic reduction of the product (3-4) affords ampicillin (3-5) [4]. An analogous scheme leads to amoxycillin (3-6), a widely used dmg that is reasonably well absorbed on oral administration. 

The key sequence in a somewhat involved stereospecihc total synthesis of a carbacephem starts by preparation of a chiral auxiliary. It is interesting to note that nitrogen is the only atom from this molecule retained in the hnal product. Constmction of this moiety starts with the formation of the carbethoxy derivative (37-2) from L(- -)-phenylglycine (37-1). Selective reduction of the free carboxyl group with borane. THF leads to the hydroxycarbamate (37-3). In a one-pot sequence, this is first cyclized to the corresponding oxazolidinone (37-4) by means of sodium hydride and then alkylated with ethyl bromoacetate (37-5). Saponification of the side chain then affords the chiral acetic acid (37-6). The carboxyl group is then activated by conversion to its acid chloride (37-7). 

Lactams.1 The ketene derived from (S)-phenyloxazolidylacetyl chloride (1), prepared from (S)-phenylglycine, undergoes cycloaddition with N-benzyl al-dimines to give two as-azetidinones with high stereochemical control (equation I). The chiral auxiliary and the benzyl group are cleaved by Birch reduction to provide enantiomerically pure azetidinones (3). 

Acetoxy-l-acetylproline, 251 L-a-Amino-y-butyrolactone, 207 /-Butyl hydroperoxide-Dialkyl tar-trate-Titanium(IV) isopropoxide, 51 (Camphorylsulfonyl)oxaziridines, 64 Cumene hydroperoxide-Dialkyl tar-trate-Titanium(IV) isopropoxide, 52 Diisobutylaluminum hydride-Tin(II) chloride-(S)-1 -[ 1 -Methyl-2-pyrroii-dinyl]methylpiperidine, 116 (S)-Phenylglycine, 225 L-Valine, 226 Crown ethers Benzo-14-crown-4, 143 12-Crown-4, 167 12-Crown-6, 218... 

The original Strecker procedure is the reaction of an aldehyde with ammonia and then with hydrogen cyanide to form the a-amino nitrile. This intermediate may also be obtained by reacting the aldehyde cyanohydrin with ammonia, but a more convenient method is to treat the aldehyde in one step with ammonium chloride and sodium cyanide. The a-amino acid is obtained when the amino nitrile is hydrolysed under either acidic or basic conditions the former are usually preferred. The preparation of a-phenylglycine (R = Ph) from benzalde-hyde is typical of the general procedure (cognate preparation in Ept 5.181). 

The first ionically bonded phase was presented by Pirkle it contained (/ )-3,5-dinitrobenzoyl phenylglycine [13]. The most commonly used 7t-acid moiety is the 3,5-dinitrophenyl group introduced by the reaction of 3,5-dinitrobenzoyl chloride (DNB-C1) on chiral selectors such as amino acids, amino alcohols, and amines. In addition, pentafluorobenzoyl derivatives have also been reported [14,15]. The 7r-basic phases are complimentary to the re-acidic phases. These CSPs include the presence of phenyl- or alkyl-substituted phenyl groups. Macaudiere et al. [9] designed a CSP containing both re-acidic and re-basic... 

Benzyloxycarbonyl chloride Dicyclohexylcarbodiimide N-Hydroxysuccinimide p-Hydroxy-D-phenylglycine Citric acid... 

Transamination. Transamination with pyridoxal or analogs requires a metal catalyst such as Cu(II). However, transamination can be effected with DPL in combination with hexadecyltrimethylammonium chloride. By using these two reagents phenylglycine undergoes transamination with 2-oxoglutaric acid (equation I). 

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