Glycine ethyl esters

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. 

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]-... 

L-phenylalanyl L-phenylalanine methyl ester L-prolyl L-alanine methyl ester L-prolyl L-aspartic dibenzyl ester L-prolyl glycine ethyl ester L-prolyl methyl ester L-serylglycine ethyl ester... 

A solution of 140 g. (1 mole) of glycine ethyl ester hydrochloride 1 and 3 g. of sodium acetate in 150 ml. of water is added to the flask and cooled to 2° by means of an ice-salt bath. A cold solution of 80 g. (1.15 moles) of sodium nitrite in 100 ml. of water is added, and the mixture is stirred until the temperature has fallen to 0°. The temperature is maintained below 2°, and stirring is continued throughout all the following operations. To the cold mixture are added 80 ml. of cold, alcohol-free ethyl ether (Note 1) and 3 ml. of cold 10% sulfuric acid. After 5 minutes, the reaction mixture is blown over into the 1-1. separatory funnel by application of air pressure. The lower aqueous layer is quickly sucked back into the reaction flask. The ether layer is removed and immediately washed with 50 ml. of cold 10% sodium carbonate solution. This ether solution should be neutral to moist lilmus paper if not, the washing with sodium carbonate is repeated. The ether solution is finally dried over 10 g. of anhydrous sodium sulfate. 

Ethyl diazoacetate has been prepared by the action of sodium nitrite on glycine ethyl ester hydrochloride.3... 

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