1,2-Dichloroethane → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-hydroxy-5-(2-oxopyrrolidin-1-yl)-benzamide

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Reaction Steps

To a stirred solution of 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid (D6) (0.449 g, 2.03 mmol), EDC (0.389 g, 2.03 mmol) and HOBT (0.311 g, 2.03 mmol) in DMF (8 ml) was added (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)amide (D2(0.50 g, 1.56 mmol). After stirring for 20 hrs at room temperature, the DMF was evaporated and ethyl acetate and water were added. The product was extracted into ethyl acetate and the combined extracts were washed with 2N HCl, saturated aqueous sodium bicarbonate solution and brine and then dried over sodium sulfate and evaporated. Purification by column chromatography on silica gel (elution with 2–5% methanol in dichloromethane) gave the product, 0.588 g.

Provenance & Evidence