[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[Cl-].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C@@H:21]([NH3+:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C@H:21]([NH:28][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([Br:1])[CH:3]=1)[CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[Cl:13])[CH3:27]3-Bromo-4-methylbenzoic acid (331 mg, 1.5 mmol, 1.0 eq.) and (R)-2-(2-chloro-phenyl)-1-ethoxycarbonylmethyl-ethyl-ammonium chloride (428 mg, 1.5 mmol, 1.0 eq.) were combined with DIPEA (844 μL, 3.2 eq.) and HATU (585 mg, 1.5 mmol, 1.0 eq.) in DCM (8 mL). The resulting mixture was stirred for 1 hour, then chromatographed (0-80% EtOAc/hexanes gradient) to yield (R)-3-(3-bromo-4-methyl-benzoylamino)-4-(2-chloro-phenyl)-butyric acid ethyl ester.
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