Cysteamine → S-Tritylcysteamine

Participants

Reaction Steps

A solution of 2-aminoethanethiol.HCl 80 (11.4 g, 100 mmol), triphenylmethanol (TrOH, 26.0 g, 100 mmol) in HCl (37%, 44.8 mL) and acetic acid (280 mL) was stirred for 5 h at 40° C. The reaction mixture was concentrated in vacuo and the resulting white solid was washed with ether and dissolved in H2O/CH2Cl2 (1:1). After adjusting the pH of the aqueous layer to ca. 14 with 1 N NaOH, the desired compound was removed by extraction. The combined organic layers were dried (K2CO3), filtered, and concentrated in vacuo to provide a white solid, S-(triphenylmethyl) 2-aminoethanethiol (28.8 g, 90.0 mmol, 90% from 80). Rf =0.50 (1:9 MeOH/CH2Cl2); 1H NMR (DMSO-d6) δ7.35-7.20 (m, 15H), 2.43 (t, J=6.1, 2H), 2.15 (t, J=5.9, 2H). To a solution of S-(triphenylmethyl) 2-aminoethanethiol (3.00 g, 9.40 mmol) and triethylamine (951 mg, 9.40 mmol) in dry CH2Cl2 (30 mL) was added bromoacetyl bromide (1.90 g, 9.40 mmol) over 15-20 min at -20°. The reaction mixture was stirred at -20° for 30 min and at room temperature for 1 h. To this mixture was added an additional equivalent of S-(triphenylmethyl) 2-amninoethanethiol (3.00 g, 9.40 mmol) and triethylamine (951 mg, 9.40 mmol). After stirring for 16 h at room temperature, the reaction mixture was concentrated under reduced pressure. The crude product was purified by flash chromatography (1:99 MeOH/CH2Cl2) to give compound 81 as a white foam (4.64 g, 6.95 mmol, 67% from amine 80). Rf 0.60 (1:9 MeOH/CH2Cl2); 1H NMR (DMSO-d6) δ7.77 (t, J=6.1, 1H), 7.35-7.20 (m, 30H), 2.97 (dd, J=6.0, 5.9, 2H), 2.86 (s, 2H), 2.35 (t, J=6.1, 2H), 2.18 (m, 4H). See Photaki et al., J. Chem. Soc. (c) 2683-2687 (1970); Bryson, N. J., Neutral technetium (v) complexes with N,S-donor chelates. Ph.D. thesis, Massachusetts Institute of Technology, Cambridge, Mass. (1988).

Provenance & Evidence