Reaction SMILES: [CH2:1]([N:3]([CH2:50][CH3:51])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[C:12]2[CH:29]=[CH:28][CH:27]=[C:14]([C:15]([N:17]([CH3:26])[CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[O:16])[CH:13]=2)=[C:6]([C:31]2[CH:36]=[C:35]([C:37](=[O:49])[NH:38][C@@H:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH2:42][CH2:41][CH2:40]3)[CH:34]=[CH:33][N:32]=2)[CH:5]=1)[CH3:2].[C:52](=O)([O:76]C1C=CC([N+]([O-])=O)=CC=1)[O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH3:75]>C(#N)C.CN(C)C1C=CN=CC=1>[CH2:50]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:12]2[CH:13]=[C:14]([CH:27]=[CH:28][CH:29]=2)[C:15]([N:17]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:52]([O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH3:75])=[O:76])[CH2:22][CH2:21]2)[CH3:26])=[O:16])=[O:30])=[C:6]([C:31]2[CH:36]=[C:35]([C:37](=[O:49])[NH:38][C@@H:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH2:42][CH2:41][CH2:40]3)[CH:34]=[CH:33][N:32]=2)[CH:5]=1)[CH3:51]
Reactant: COCCOCCOCCOCCOCCOCCOCCOC(=O)Oc1ccc([N+](=O)[O-])cc1
Reactant: CCN(CC)c1ccc(NC(=O)c2cccc(C(=O)N(C)CCN3CCNCC3)c2)c(-c2cc(C(=O)N[C@H]3CCCc4ccccc43)ccn2)c1
Agent: CN(C)c1ccncc1
Solvent: CC#N
Product: CCN(CC)c1ccc(NC(=O)c2cccc(C(=O)N(C)CCN3CCN(C(=O)OCCOCCOCCOCCOCCOCCOCCOC)CC3)c2)c(-c2cc(C(=O)N[C@H]3CCCc4ccccc43)ccn2)c1
Temperature: 90 °C
Reaction time: 5 h
Yield: 36.9 %

Procedure:
This compound was prepared according to the procedure described for the synthesis of Example 214 substituting 212b in place of 213c. Into a 8-mL sealed tube, was placed a solution of (S)—N1-(4-(diethylamino)-2-(4-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-(piperazin-1-yl)ethyl)isophthalamide (150 mg, 0.22 mmol, 1.00 equiv) in acetonitrile (5 mL), 2,5,8,11,14,17,20-heptaoxadocosan-22-yl 4-nitrophenyl carbonate (165 mg, 0.33 mmol, 1.50 equiv), 4-dimethylaminopyridine (53 mg, 0.43 mmol, 2.00 equiv). The resulting solution was stirred for 5 h at 90° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 10 ml of water. The resulting solution was extracted with 3×30 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 3×30 mL of NH4Cl aq. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (100 mg) was purified by Prep-HPLC with the following conditions (1#-UV1-SHIMADZU-SPD-20A): Column, SunFire Prep C18, 19*150 mm 5 um; mobile phase, water with 0.05% TFA and CH3CN (30% CH3CN up to 50% in 6 min); Detector, Waters2545 UvDector 254&220 nm. 85.6 mg product was obtained. This resulted in 85.6 mg (28%) of (S)-2,5,8,11,14,17,20-heptaoxadocosan-22-yl 4-(2-(3-(4-(diethylamino)-2-(4-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)-N-methylbenzamido)ethyl)piperazine-1-carboxylate as a yellow solid. LC-MS (ES, m/z): 1055 [M+H]+ H-NMR (300 MHz, CD3OD, ppm): 8.92 (d, J=5.1 Hz, 1H), 8.60 (s, 1H), 8.35 (s, 1H), 8.13 (t, J=7.5 Hz, 2H), 7.69-7.85 (m, 4H), 7.44-7.46 (m, 1H), 7.26 (d, J=6.6 Hz, 1H), 7.14-7.19 (m, 3H), 5.38 (s, 1H), 4.26-4.86 (m, 3H), 3.99 (s, 2H), 3.63-3.74 (m, 31H), 3.52-3.61 (m, 6H), 3.31-3.34 (m, 5H), 3.09-3.12 (m, 3H), 2.84-2.91 (m, 2H), 1.90-1.97 (m, 4H), 1.21-1.26 (m, 6H).