Sodium carbonate (Na2CO3, 5 mmol) was added to a solution of 4-hydroxyproline (5 mmol) in water (15 mL) with continuous stirring until all the solutes dissolved. The solution was cooled to − 5 °C and 4-nitrobenzenesulfonyl chloride (5 mmol) was added in four portions over a period of 1 h. The reaction mixture was further stirred at room temperature for 4 h(Scheme 1). The mixture was acidified using 20% HCl until a pH of 2 was obtained. The white product obtained was filtered, washed, and dried in the open air. Yield (1.12 g, 71.34%), MP = 190–192 °(O), 1004 (C–N), 685 (S–N). 1H-NMR (DMSO, 400 MHz) δ: 8.40 (m, 2H, ArH), 8.10 (m, 2H, ArH), 4.87 (s, 1H, OH exchangeable with HDO), 4.31 (m, 2H, CH-CO2H and CH-OH), 3.59 (dd, 1H, CHa of CH2-CH-CO2H, J = 8.00, 4.00 Hz) 3.41 (dt, 1H, CHb of CH2-CH-CO2H, J = 8.00, 4.00 Hz), 2.19 (ddt, 1H, CH of CH2-N, J = 12.00, 8.00, 4.00 Hz), 2.06 (ddd, 1H, CHb of CH2-N, J = 12.00, 8.00,4.00 Hz).13C NMR (DMSO, 100 MHz) δ: 174.19 (C = O), 150.28, 143.40, 128.81, 123.79 (4 aromatic carbons), 69.21, 59.94, 56.51, 39.00 (4 aliphatic carbon). DEPT (100 MHz) δ: 174.19, 150.28, 143. 40 (tertiary C), 128.81, 123.79, 69.21, 59.94 (CH carbons), 56.51 and 39.00 (CH2 carbons).
Ugwu D.I., Eze F.U., Ezeorah C.J., Rhyman L., Ramasami P., Tania G., Eze C.C., Uzoewulu C.P., Ogboo B.C, & Okpareke O.C. (2023). Synthesis, Structure, Hirshfeld Surface Analysis, Non-Covalent Interaction, and In Silico Studies of 4-Hydroxy-1-[(4-Nitrophenyl)Sulfonyl]Pyrrolidine-2-Carboxyllic Acid. Journal of Chemical Crystallography.