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4-(BENZYLAMINO)-4-OXOBUTANOIC ACID synthesis

5synthesis methods
-

Yield:64984-60-7 94%

Reaction Conditions:

in toluene at 0; for 1 h;

Steps:

5.1.10. 4-Oxo-4-[(phenylmethyl)amino]butanoic acid

A solution of benzylamine (0.20 g, 1.87 mmol) in anhydroustoluene (6 mL) was added to a solution of succinic anhydride(0.19 g, 1.87 mmol) in anhydrous toluene (14 mL) at 0 C and themixture was stirred at the same temperature for 1 h. Then, solidswere filtered off washed with cold toluene and dried. Obtainedcrude 16 (0.37 g, 94%) was used successively without further purification:mp 127e130 C. IR (KBr) cm1 3299, 2918, 1693, 1640,1546, 1231, 734, 660; 1H NMR (DMSO-d6): d 8.37 (t, J 6.0 Hz, 1H,NH which exchanges with D2O), 7.42e7.18 (m, 5H, aromatic), 4.26(d, J 6.0 Hz, 2H, C6H5CH2), 2.44e2.38 (m, 2H 2H, CH2CH2COOH).

References:

Romeo, Giuseppe;Salerno, Loredana;Pittalà, Valeria;Modica, Maria N.;Siracusa, Maria A.;Materia, Luisa;Buccioni, Michela;Marucci, Gabriella;Minneman, Kenneth P. [European Journal of Medicinal Chemistry,2014,vol. 83,p. 419 - 432]

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