[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([NH2:21])[CH2:19][CH3:20].O1CCCC1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](=[O:13])[NH:21][CH2:18][CH2:19][CH3:20])([CH3:2])([CH3:3])[CH3:4]2-tert-Butoxycarbonylamino-benzoic acid (1.00 g, 0.00421 mol) and 1-Propanamine (0.249 g, 0.00421 mol) were dissolved in Tetrahydrofuran (10.0 mL, 0.123 mol) and the mixture was treated with N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.808 g, 0.00421 mol) and 1-Hydroxybenzotriazole (0.570 g, 0.00421 mol). The reaction was then allowed to stir overnight at room temperature. The reaction mixture was poured over saturated sodium bicarbonate, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 1.17 grams (49%) of (2-Propylcarbamoyl-phenyl)-carbamic acid tert-butyl ester.
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