Glycinates ethyl

N-Benzoyl L-leucylglyclne ethyl ester (3). N-Benzoy-L-leucine 1 (0.235 g, 1 mmol) and glycine ethyl ester hydrochloride 2 (0 1534 g, 1.1 mmol) in OMF (10 mL) under stirring vyas treated with diethylphosphoryl cyanide 3 (0.179 g, 1.1 mmol) In OMF at 0°C, followed by the addition of triethylamine (0.212 g, 2 1 mmoO. The mixture was stirred for 30 min at 0°C and 4 h at 20 C The reaction mixture was diluted with PhH-EtOAc, washed with 5% HCI, water, 5% NaHCOs solution and bnne. Evaporation of the solvent gave crude 4 which after sIDca gel chromatography afforded 0.271 g of 4 (66%) (pure L), mp 1S8-160°C. 

Glycine ethyl ester hydrochloride has been prepared by the action of absolute alcohol and hydrogen chloride on glycine from glycyl chloride and alcohol by the action of ammonia or hexamethylenetetramine on chloroacetic acid, and subsequent hydrolysis with alcoholic hydrochloric acid and by the action of hydrogen chloride and alcohol on methyleneamino-acetonitrile. ... 

Glycine ethyl ester hydrochloride [623-33-6] M 136.9, m 145-146", pK 7.69. Crystd from absolute EtOH. 

Bromelain (anti-inflammatory Ananase from pineapple) [37189-34-7] Mr 33 000, [EC 3.4.33.4]. This protease has been purified via the acetone powder, G-75 Sephadex gel filtration and Bio-Rex 70 ion-exchange chromatography and has Aj 20.1 at 280nm. The protease from pineapple hydrolyses benzoyl glycine ethyl ester with a Km (app) of 210mM and kcat of 0.36 sec. [Murachi Methods Enzymol 19 273 1970 Balls et al. nd Eng Chem 33 950 1941.]... 

Enantiomerically pure dipeptide is obtained when the /7-nitrophenyl ester of N-henzoyl-L-leueine is coupled with glycine ethyl ester in ethyl acetate ... 

If, however, the /7-nitrophenyl ester of iV-henzoyl-L-leucine is treated with 1-methyl-piperidine in chloroform for 30 min and then coupled with glycine ethyl ester, the dipeptide isolated is almost completely racemic. Furthermore, treatment of the p-nitrophenyl ester of iV-benzoyl-L-leucine with 1-methylpiperidine alone leads to the formation of a crystalline material, C13H15NO2, having strong IR bands at 1832 and 1664 cm . Explain these observations, and suggest a reasonable stmcture for the crystalline product. 

Aminobenzophenone Glycine ethyl ester hydrochloride Nitric acid... 

A mixture of 16.8 g of 2-aminobenzophenone, 11.9 g of glycine ethyl ester hydrochloride and 200 cc of pyridine was heated to reflux. After one hour, 20 cc of pyridine was distilled off. The solution was refluxed for 15 hours, then 11.9 g of glycine ethyl ester hydrochloride was added and the refluxing was continued for an additional 4 hours. The reaction mixture was continued for an additional 4 hours. The reaction mixture was concentrated in vacuo, then diluted with ether and water. The reaction product, 5-phenyl-3H-1,4-benzodiazepin-2(1 H)-one, crystallized out, was filtered off, and then recrystallized from acetone in the form of colorless rhombic prisms, MP 182°Cto 183°C. 

Glycine ethyl ester hydrochloride, 14, 46 16, 86 17, 92 Grignard reaction in -butyl ether, 11, 84 with acetaldehyde, 12, 48 with butyl p-toluenesulfonate, 10, 4 with carbon dioxide, 11, 80 with dimethyl sulfate, 11, 66 with ethyl carbonate, 11, 98... 

Glycine ethyl ester hydrochloride, methyl formate, and triethylamine were purchased from Aldrich Chemical Company, Inc., and were used without purification. 

Storage stability Extremely unstable in presence of trace metals or other impurities. Traces of iron chloride may cause explosive decomposition. Pure material is stable for only 1 or 2 months. It may be stabilized by nitromethane, chloropicrin, glycine, ethyl acetate, or ether - but only in glass vessels below 20°C. Apparently, it is most stable in aromatic solvents. 

N-[N-(benzyloxycarbonyl)-L-aspart-l-oyl-(L-alanyl-L-threonyl-L-leucyl-L-alanine p-nitrobenzyl ester)-4-oyl]-N-[N-(benzyloxycarbonyl)-L-aspart-l-oyl-(L-alanyl-L-threonyl-L-leucyl-L-alanyl-L-serine p-nitrobenzyl ester)-4-oyl]-N-[N-(benzyloxycarbonyl)-L-aspart-1 -oyl-(glycine ethyl ester)-4-oyl -N-[N-(benzyloxycarbonyl)-L-aspart-l-oyl-(glycyl-L-serine methyl ester)-4-oyl]-... 

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