Hydrochloric Acid → N-hydroxy-5-[(2-phenyl-4-thiazolyl)methoxy]-1-(phenylmethyl)-N,2-dimethyl-1H-indole-3-acetamide

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Reaction Conditions

Reaction Steps

A mixture of the compound of Example 40 (1.0 g, 2.13 mmol), methylene chloride (50 mL) and dimethylacetamide (0.15 mL) is cooled to 5° C. and with stirring, a solution of oxalyl chloride (0.45 mL, 5.3 mmol) in methylene chloride (10 mL) is added slowly. After stirring at room temperature for 30 minutes, the reaction mixture is poured into a solution containing tetrahydrofuran (11 mL), water (1.1 mL), triethylamine (1.8 mL) and N-methylhydroxylamine hydrochloride (0.7 g, 8.5 mmol). After stirring at room temperature for 1 hour, the reaction mixture is diluted with methylene chloride (150 mL), poured into 2N HCl (150 mL) and the layers are separated. The aqueous layer is washed again with methylene chloride (100 mL). The combined methylene chloride extract is washed with water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated under reduced pressure to give 1.0 g of a crude solid. The solid is recrystallized from ether/methylene chloride to give 0.6 g of white crystalline product in 57 % yield, m.p. 171°-173° C.

Provenance & Evidence