1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Nitro-4-tert-butyl-N-(2,2-diethoxy-ethyl)-benzamide

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Reaction Steps

2-nitro-4-tert-butylbenzoic acid (1.5 g, 7 mmol, prepared according to J. Am. Chem. Soc, 1955, 77, 5441) was stirred in THF at room temperature, 1.7 mL diisopropylethyl amine (13 mmol, 2 eq) was added, followed by 984 mg (7.7 mmol, 1.1 eq) 2-amino acetaldehyde diethylacetal. (3-Dimethylamino-propyl)-ethyl-carbodiimide (1.55 g, 8 mmol, 1.2 eq) was added, followed by a catalytic amount (ca. 50 mgs) hydroxybenzotriazole hydrate. The mixture was stirred at room temperature for 16 hours, diluted with water, extracted with diethyl ether 3×, the ether layers were washed with water, brine, and dried over MgSO4. Removal of solvent under vacuum, followed by chromatography on silica gel, eluting with 25% ethyl acetate in hexanes, gave the title compound 0.950 g, (M+H)+=224.

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