OC(C1CCN(CC2C=CC([N+]([O-])=O)=C(N[C@@H:19]3[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=O)[CH2:21][CH2:20]3)C=2)CC1)(C)C.C1N=C[N:33](C(N2C=NC=C2)=O)C=1.[OH-].[NH4+]>CN(C=O)C>[CH:22]1([C:25]([NH2:33])=[O:27])[CH2:23][CH2:24][CH2:19][CH2:20][CH2:21]1To a solution of cis-4-(5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)cyclohexanecarboxylic acid (0.53 g, 1.263 mmol) in DMF (7 mL) was added CDI (0.410 g, 2.53 mmol) and aqueous ammonium hydroxide (100 μL, 2.53 mmol). The reaction was stirred overnight at RT. After 16 hours, the reaction mixture was partitioned between water and DCM and the aqueous layer was extracted with DCM. The combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography, eluting with 0-100% (90:9:1 DCM/MeOH/NH4OH)/DCM, to provide cis-4-(5-(4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)cyclohexane-carboxamide as an orange foam (0.213 g, 40.3% yield). MS, m/z (C22H34FN4O4): calcd, 418.3. found, 419.1 [M+H].
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