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ChemicalBook CAS DataBase List (+/-)-N-(BENZYLIDENE)ALANINE ETHYL ESTER
60930-36-1

(+/-)-N-(BENZYLIDENE)ALANINE ETHYL ESTER synthesis

2synthesis methods
-

Yield:60930-36-1 92.2%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 25; for 5 h;Product distribution / selectivity;

Steps:

1

Example 1 ethyl 2-(1-phenylmethylidene)aminopropionate 353.3 g of alanine ethyl ester hydrochloride and 150 g of benzaldehyde were suspended in 2 l of CH2Cl2 and then admixed dropwise at 0° C. with 232.7 g of triethylamine. The suspension was warmed to 20-25° C. and stirred for another 5 h. The precipitate was filtered off, with CH2Cl2 washed and discarded. The organic phase was washed with water, dried and freed of the solvent. 632.7 g of the title compound were obtained. Purity 97% (GC); yield: 92.2%. 1H NMR (CDCl3): 1.3 ppm (t, 3H, CH3); 1.55 ppm (s, 3H, CH3); 4.15 ppm (d, 1H, CH); 4.2 ppm (m, 2H, OCH2); 7.4 ppm (m, 3H, arom. H); 7.8 ppm (m, 2H, arom. H); 8.3 ppm (s, 1H, CH=N).

References:

US2011/144336,2011,A1 Location in patent:Page/Page column 7