Reaction SMILES: [CH3:1][NH:2][C:3]([NH:5][S:6]([C:9]1[CH:28]=[CH:27][C:12]([O:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[C:15](O)=[O:16])=[C:11]([CH2:29][CH2:30][CH3:31])[CH:10]=1)(=[O:8])=[O:7])=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:44]([C:47]1[CH:52]=[CH:51][C:50]([S:53]([NH2:56])(=[O:55])=[O:54])=[CH:49][CH:48]=1)([CH3:46])[CH3:45].C1CCN2C(=NCCC2)CC1>O1CCCC1.C(Cl)(Cl)Cl.CO.C(O)(=O)C>[CH:44]([C:47]1[CH:48]=[CH:49][C:50]([S:53]([NH:56][C:15](=[O:16])[CH:14]([C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[O:13][C:12]2[CH:27]=[CH:28][C:9]([S:6]([NH:5][C:3](=[O:4])[NH:2][CH3:1])(=[O:7])=[O:8])=[CH:10][C:11]=2[CH2:29][CH2:30][CH3:31])(=[O:54])=[O:55])=[CH:51][CH:52]=1)([CH3:46])[CH3:45]
Reactant: CCCc1cc(S(=O)(=O)NC(=O)NC)ccc1OC(C(=O)O)c1ccc2c(c1)OCO2
Reactant: CC(C)c1ccc(S(N)(=O)=O)cc1
Agent: O=C(n1ccnc1)n1ccnc1
Solvent: C1CCC2=NCCCN2CC1
Solvent: ClC(Cl)Cl
Solvent: CC(=O)O
Product: CCCc1cc(S(=O)(=O)NC(=O)NC)ccc1OC(C(=O)NS(=O)(=O)c1ccc(C(C)C)cc1)c1ccc2c(c1)OCO2
Temperature: 25 °C

Procedure:
A solution of 384 mg (0.853 mmol) of the product of Step B and 208 mg (1.28 mmol) of 1,1'-carbonyldiimidazole in 2 mL of dry tetrahydrofuran was refluxed 2 minutes by placing the reaction mixture into a preheated oil bath. After brief refluxing and gas evolution, TLC analysis (90:10:1 chloroform/methanol/acetic acid) indicated that the desired intermediate had formed. The reaction mixture was then cooled to room temperature and 255 mg (1.28 mmol) of dry 4-iso-propylbenzenesulfonamide, 10 mg (0.085 mmol) of CDI followed by 191 μL (1.28 mmol) of DBU was added. The reaction mixture was refluxed for 3 minutes, allowed to cool and stir at room temperature 1 hour after which TLC analysis (96:3:1 chloroform/methanol/acetic acid) indicated the desired product had been formed. The reaction mixture was poured into 10% citric acid and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was partially purified by silica-gel flash chromatography eluting first with ethyl acetate and then with (92:7:1 chloroform/methanol/acetic acid). The purified fractions were combined to afford 48 mg (9%) of the title compound. Upon standing, material precipitated from the ethyl acetate fractions to afford an addition 55 mg (10%) of the title compound. The remainder of semi-purified material was combined and purified using a Waters Delta Prep 4000 HPLC applying the residue in 6 mL total volume (4.5 mL methanol and 1.5 mL water) to an M1000 Prep-Pak module containing a 47×300 mm 15 μM DeltaPak C18 column and eluting isocratically at 50 mL/min using 60% A (95-5 acetonitile-water) and 40% B (95-5 water-acetonitrile) each with 0.1% TFA. The column effluent was monitored simultaneously at 210 and 277 nM with a Waters model 490 UV-visible detector and the purified fractions were combined in a round bottom flask, frozen in a -78° C. dry ice-acetone bath and lyophylized. The HPLC purified lyophylizate 155 mg (29%), the silica gel purified amorphous solid 48 mg (9%) and the precipitated amorphous solid 55 mg (10%) were combined to afford 258 mg (48%) of the title compound.