Acetylglycine

Azlactone of a-acetylaminocinnamic acid. Warm a mixture of 29 g. of acetylglycine, 39-5 g. (37 -5 ml.) of redistilled benzaldehyde (Section IV,115), 15 g. of anhydrous sodium acetate and 67 g. (62 ml.) of acetic anhydride (95 per cent.) in a 500 ml. conical flask (equipped with a reflux condenser) on a water bath with occasional stirring until solution is complete (10-20 minutes). Boil the resulting solution for 1 hour, cool and leave in a refrigerator overnight. Stir the sohd mass of yellow crystals with 60 ml. of cold water, transfer to a Buchner funnel and wash well with cold water. (If the odour of benzaldehyde is stih apparent, wash with a little ether.) Recrystallise from carbon tetrachloride or from ethyl acetate-hght petroleum. The yield of azlactone, m.p. 150°, is 35 g. 

Thiazolecarboxaldehydes exhibit many reactions typical of aldehydes. However, they give no aldolization reaction (no a-hydrogen), but they do react with different compounds such as acetic anhydride, hippuric acid, acetylglycine, and so for (37, 101, 102). Thus 2-phenyl-4-fonnylthiazole (31) mixed with hippuric acid and treated with AcOa and anhydrous NaOAc gives the azalactone (32) (Scheme 32). 

N-Acetylglycine [543-24-8] M 117.1, m 206-208 , pKf-1.92, pKi 3.69. Treated with acid-washed charcoal and recrystd three times from water or EtOH/Et20 and dried in vacuo over KOH [King and King J Am Chem Soc 78 1089 1956],... 

CH3C CH2C02H + CH3C02H A -Acetylglycine (89-92%) Acetic acid... 

Table 19 also describes polyphosphazenes bearing oligopeptide side chains (Gly-Pro-Gly and Gly-Val-Ala tripeptides) [636], potentially useful for tissue engineering, and polymers bearing AT-acetylglycine substituents [637]. The... 

Figure 16 shows the 13C spectra of N-acetylglycine obtained from the traces of the indirectly detected dimension of the HSQC experiment. The spectrum... 

The range of products formed on gamma radiolysis of N-acetylglycine was similar to that formed on radiolysis of the aliphatic carboxylic acids, but there are some noticeable differences in the yields of products. Carbon dioxide is by far the major volatile product of radiolysis and the corresponding product of the decarboxylation reaction, N-methyl acetamide, is also present in large yield, but the yield of this product was not quantitatively determined. By contrast, carbon monoxide is found in very small yield. The yield of acetamide, the product of N-Ca bond scission, is found in much greater yield. 

Table IV. G-values for the volatile products formed on gamma radiolysis of N-acetylglycine at 303 K...

Methoxyacetic acid A-Acetylglycine Glycolic acid Formic acid Acetic acid Malonic acid Succinic acid o-Phosphoric acid Citric acid ACN... 

Acetonitrile, 407 Acetophenone, 725,729,730 phenylhydrazone, 852 p-Acetotoluidide, 593, 605 Acetoxime, 343 Acetylacetone, 861, 862, 863 Acetylation, reductive, 749 Thiele, 749 Acetyl chloride, 367 2-Acetylcyciohexanone, 862, 864 Acetylene, 245, 897 reactions of, 245, 246 Acetylenic compounds, synthesis of, 467-469, 895-902 Acetylglycine, 909 Acetylmethylurea, 968, 969 Acetylsalicylio acid, 996 Acetyl-o-toluidide, 578 2-Acetylthiophene, 837 Acid anhydrides of aliphatic carboxylic acids, 371... 

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