Chemical Properties
White to yellow crystalline powder
Uses
Boc-Cys(Trt)-OH is used in method for preparing ularitide.
reaction suitability
reaction type: Boc solid-phase peptide synthesis
Synthesis
General procedure for the synthesis of N-tert-butoxycarbonyl-S-trityl-L-cysteine from di-tert-butyl dicarbonate (Boc2O) and S-trityl-L-cysteine: S-trityl-L-cysteine (5 g, 12.7 mmol) was dissolved in 2N NaOH solution (80 mL), followed by the addition of di-tert-butyl dicarbonate (4.5 g, 20 mmol) . The reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the aqueous solution was acidified to pH 2 with concentrated hydrochloric acid and then extracted with dichloromethane (2 x 100 mL). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target compound N-tert-butoxycarbonyl-S-trityl-L-cysteine (5.3 g, 90% yield) as a white foamy solid without further purification.1H NMR (DMSO-d6) δ: 1.37 (s, 9H, tert-butyl-CH3); 2.29-2.58 (m , 2H, CH2); 3.76-3.79 (m, 1H, CH); 6.84 (d, J=7.8Hz, 1H, NH); 7.14-7.38 (m, 15H, triphenylmethyl-H).MALDI-TOF MS: m/z 464.8 [M+H]+, molecular weight 463.59 for calculated value C27H29NO4S.
References
[1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 383 - 392
[2] Chemical Communications, 2013, vol. 49, # 92, p. 10808 - 10810
[3] Patent: CN106432014, 2017, A. Location in patent: Paragraph 0096; 0100; 0101; 0102; 0142; 0146; 0147; 0148
[4] Patent: WO2009/137251, 2009, A2. Location in patent: Page/Page column 30; 31
[5] Chemistry of Natural Compounds, 1979, vol. 15, p. 471 - 476
