Compound 1
Tetrasodium 3-{[14,15,50,51-tetramethyl- 26,30,34,38,49,52,53,54- octaoxo-19,22,45-tris(3-sulfonatopropoxy)-1,3,6,8,11,13,16,25,27, 29,31,33,35,37,39,48-hexadecaazapentadecacyclo[37.10.2.13,6.18,11 .113,16.04,35.05,33.09,31.010,29.014,27.015,25.018,23.037,50.041,46.048,51 ]tetrapentaconta-18(23),19,21,41(46),42,44-hexaen-42-yl]oxy}propane-1-sulfonate
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InChIKey VJSHHZXHHKEPCT-COPHJLSRSA-J
Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
A solution of 5 (76 g, 97 mmol) in TFA (700 mL) was treated with 8 (154 g, 387 mmol). The mixture was stirred and heated at 70 °C for 3 h. The solvent was removed by rotary evaporation and the solid was dried in high vacuum. The solid was washed with the mixture of water and acetone (1:2, v/v, 1.5 L × 2). The solid was dissolved in water (500 mL) and adjusted to pH = 7 by adding 1 M aqueous NaOH. The solvent was removed by rotary evaporation and then the solid was further dried under high vacuum to yield 1 as a white solid (60 g, 40%). M.p. > 320 °C (dec.). IR (ATR, cm-1): 3000w, 1711s, 1456s, 1313m, 1225s, 1178s, 1076s, 972m, 920m, 822m, 797s, 756m, 665m. 1H NMR (400 MHz, D2O): 6.72 (s, 4H), 5.50 (d, J = 15.2, 2H), 5.38 (d, J = 15.7, 4H), 5.31 (d, J = 9.0, 2H), 5.25 (d, J = 8.9, 2H), 5.19 (d, J = 16.2, 4H), 4.10 (d, J = 11.1, 4H), 4.06 (d, J =11.7, 4H), 3.97 (d, J = 15.4, 2H), 3.91 (m, 4H), 3.79 (m, 4H), 2.98 (m, 8H), 2.06 (m, 8H), 1.64 (m, 6H), 1.61 (s, 6H). 13C NMR (100 MHz, D2O, 1, 4-dioxane as internal reference): δ 157.5, 157.3, 150.8, 128.3, 115.3, 79.7, 78.6, 72.3, 72.1, 69.2, 53.8, 49.4, 49.0, 35.9, 25.5, 17.1, 16.0. MS (ESI): m/z 1473.3232 ([M - H]-), calculated 1473.3216.
