[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[O:23])=[CH:18][CH:17]=2)[CH2:13][CH2:14][CH3:15])[C:9](O)=[O:10])=[CH:4][CH:3]=1.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=[N:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Br[C:66]1[CH:67]=[C:68]2[C:72](=[CH:73][CH:74]=1)[CH2:71][NH:70][CH2:69]2.CN1[C:80](=[O:81])CCC1>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:12]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[CH:20][CH:21]=2)[CH2:13][CH2:14][CH3:15])[C:9]([N:70]2[CH2:71][C:72]3[C:68](=[CH:67][CH:66]=[C:74]([C:42]4[C:41]([O:81][CH3:80])=[N:46][CH:45]=[CH:44][CH:43]=4)[CH:73]=3)[CH2:69]2)=[O:10])=[CH:6][CH:7]=1To a solution of a single stereoisomer (of the four possible) of 2-(4-chlorophenyl)-3-(4-{[(3-ethoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoic acid (EXAMPLE 1, Step C, 142 mg, 0.318 mmol) in NMP (3 mL) at room temperature was added HATU (133 mg, 0.350 mmol) and DIPEA (222 μl, 1.27 mmol). After one hour, 5-bromoisoindoline (94 mg, 0.48 mmol) was added, then the mixture was stirred at rt until the reaction was complete by LC-MS analysis. The mixture was then diluted with EtOAc then washed with water then saturated NaCl (aq). The organic layer was then dried over Na2SO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-100% EtOAc/hexanes to provide the title compound as a white solid. LC2 1.53 min. (M+H)+ 627.
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