Reaction SMILES: [C:1]([O-:4])([O-])=[O:2].[K+].[K+].[CH2:7]([N:9]([CH2:75][CH3:76])[C:10]1[CH:11]=[CH:12][C:13]([NH:36][C:37](=[O:74])[C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][C:59]([N:61]3[CH2:66][CH2:65][N:64]([C:67]4[CH:72]=[CH:71][C:70]([OH:73])=[CH:69][CH:68]=4)[CH2:63][CH2:62]3)=[O:60])[CH:39]=2)=[C:14]([C:16]2[CH:17]=[C:18]([CH:33]=[CH:34][N:35]=2)[C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[O:20])[CH:15]=1)[CH3:8].CC1C=CC(S(O[CH2:88][CH2:89][O:90][CH2:91][CH2:92][O:93][CH2:94][CH2:95][O:96][CH3:97])(=O)=O)=CC=1.O>CN(C=O)C>[C:1]([OH:4])([C:29]([F:32])([F:31])[F:30])=[O:2].[CH2:75]([N:9]([CH2:7][CH3:8])[C:10]1[CH:11]=[CH:12][C:13]([NH:36][C:37](=[O:74])[C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][C:59]([N:61]3[CH2:62][CH2:63][N:64]([C:67]4[CH:68]=[CH:69][C:70]([O:73][CH2:88][CH2:89][O:90][CH2:91][CH2:92][O:93][CH2:94][CH2:95][O:96][CH3:97])=[CH:71][CH:72]=4)[CH2:65][CH2:66]3)=[O:60])[CH:39]=2)=[C:14]([C:16]2[CH:17]=[C:18]([CH:33]=[CH:34][N:35]=2)[C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[CH:24]=2)=[O:20])[CH:15]=1)[CH3:76]
Reactant: CCN(CC)c1ccc(NC(=O)c2cccc(CCCOCCOCCOCCOCCC(=O)N3CCN(c4ccc(O)cc4)CC3)c2)c(-c2cc(C(=O)NCc3cccc(C(F)(F)F)c3)ccn2)c1
Reactant: COCCOCCOCCOS(=O)(=O)c1ccc(C)cc1
Reactant: O=C([O-])[O-]
Agent: [K+]
Solvent: CN(C)C=O
Solvent: O
Product: CCN(CC)c1ccc(NC(=O)c2cccc(CCCOCCOCCOCCOCCC(=O)N3CCN(c4ccc(OCCOCCOCCOC)cc4)CC3)c2)c(-c2cc(C(=O)NCc3cccc(C(F)(F)F)c3)ccn2)c1
Product: O=C(O)C(F)(F)F
Temperature: 70 °C
Yield: 110.4 %

Procedure:
Finely ground K2CO3 (54 mg, 039 mmol) was added to a solution of 2-(5-(diethylamino)-2-(3-(16-(4-(4-hydroxyphenyl)piperazin-1-yl)-16-oxo-4,7,10,13-tetraoxahexadecyl)benzamido)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide (125 mg, 0.13 mmol) and 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (50 mg, 0.16 mmol) in DMF (0.30 mL), and was heated at 70° C. for 3 hours with stirring. The reaction mixture was cooled to room temperature and another portion of 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (75 mg, 0.34 mmol) was added. The mixture was stirred for 3 days at room temperature and then 5 hours at 70° C. Water (10 mL) was added to the cooled reaction mixture and extracted with DCM (3×10 mL). The combined organic layers were dried (Na2SO4) and concentrated. Purification by reverse-phase HPLC eluting with a water/ACN gradient containing 0.1% TFA gave a TFA salt of the title compound (80 mg). 1H NMR (400 MHz, CD3OD, ppm) δ 9.44 (t, J=5.0 Hz, 0.6H), 8.93 (dd, JAB=5.3 Hz, JAC=0.6 Hz, 1H), 8.84 (d, J=9.0 Hz, 1H), 8.40 (s, 1H), 8.09 (d, J=2.5 Hz, 1H), 7.88 (dd, JAB=5.1 Hz. JAC=0.5 Hz, 1H), 7.80 (m, 2H), 7.69 (s, 1H), 7.65-7.52 (m, 4H), 7.47 (dd, JAB=4.1 Hz, JAC=1.2 Hz, 2H), 7.09 (d, J=9.0 Hz, 2H), 6.88 (d, J=9.2 Hz), 4.69 (d, J=4.3 Hz 2H), 4.04 (m, 2H), 3.78-3.68 (m, 12H), 3.66-3.63 (m, 2H), 3.62-3.52 (m, 16H), 3.51-3.45 (m, 4H), 3.31 (s, 3H), 3.22 (t, J=4.1 Hz, 2H), 3.16 (t, J=4.1 Hz, 2H), 2.80 (t, J=7.4 Hz, 2H), 2.64 (t, J=6.3 Hz, 2H), 1.91 (m, 2H), 1.20 (t, J=7.1 Hz, 6H). MS (ES, m/z): 1115.4 [M+H]+.