Compound 2
Tetrasodium 3-{[14,15,44,45-tetramethyl-30,34,38,42,46,60,61,62 -octaoxo-19,50,57-tris(3-sulfonatopropoxy)-1,3,6,8,11,13,16,29, 31,33,35,37,39,41,43,47-hexadecaazaheptadecacyclo[41.2.14.13,6.18,11.113,16 .04,39.05,37.09,35.010,33.014,31.015,29.018,27.020,25.041,45.044,47.0 49,58.051,56]dohexaconta-18,20,22,24,26,49,51,53,55,57-decaen-26-yl]oxy}propane-1-sulfonate
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InChIKey BVEYGKMWGAFTCE-FMXOJJLSSA-J
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
A solution of 5 (2.67 g, 3.42 mmol) in TFA (25 mL) was treated with 9 (6.13 g, 13.7 mmol). This solution was stirred and heated at 70 °C for 3 h. The solvent was removed with rotary evaporation and the solid was dried in high vacuum. The crude mixture was refluxed in EtOH (60 mL) overnight and then filtered. The solid was dissolved in hot water (20 mL). The solution was adjusted to pH = 7 with 1 M NaOH. The solution was cooled down to RT and filtered to yield 2 as a white solid (1.7 g, 30%). M.p. > 196 °C (dec.). IR (ATR, cm-1): 3433w, 1717s, 1471s, 1425m, 1383m, 1349m, 1317m, 1179s, 1082s, 1036s, 922w, 881w, 827m, 801s, 757m, 728m, 676m. 1H NMR (600 MHz, D2O): 7.72 (m, 4H), 7.27 (m, 4H), 5.48 (d, J = 15.3, 2H), 5.42 (d, J = 15.7, 4H), 5.31 (d, J = 8.9, 2H), 5.25 (d, J = 8.9, 2H), 5.12 (d, J = 16.0, 4H), 4.30 (d, J = 16.0, 4H), 4.12 (d, J = 15.7, 4H), 4.00 (m, 4H), 3.96 (d, J = 15.3, 2H), 3.74 (m, 4H), 3.08 (m, 8H), 2.13 (m, 8H), 1.66 (s, 6H), 1.61 (s, 6H). 13C NMR (125 MHz, D2O, 1, 4-dioxane as internal reference): δ 156.7, 156.3, 148.2, 127.7, 127.0, 126.1, 122.3, 78.6, 77.6, 74.1, 71.5, 71.2, 52.9, 48.5, 36.5, 25.1, 16.4, 15.2. High-Res MS (ESI): m/z 777.1986 ([M + 2H]2+), calculated 777.1972.
