Trichloroacetyl chloride → HCID 54431643, compound

Participants

Reaction Steps

The title compound is prepared by reaction of 3-(4-bromo-2-fluorobenzyl)-2-methoxyimino-4-oxooctanamide (from Step H) with trichloroacetyl chloride in the presence of triethylamine according to the procedure of Example 4, Step F. Alternatively, the following procedure is used. To 1 mmol of the amide from Step H is added about 12 mL of polyphosphate ester (PPE) [M. Cava, M. Lakshmikantham, and M. Mitchell, J. Org. Chem., 34, 2665 (1969)] solution, consisting of approximately a 2:1 ratio of PPE and CDCl3 (used as a surrogate for alcohol-free chloroform). The mixture is stirred at reflux under N2 for about 3 hours, and then the solvent is removed by concentration in vacuo. The residue is cooled in an ice bath and treated with an excess of saturated aqueous Na2CO3. The mixture is stirred for 1 hour and then extracted with ethyl acetate. The organic phase is washed further with H2O, then dried over Na2SO4, filtered, and concentrated. The residue is purified by column chromatography on silica gel (elution with hexane-EtOAc) to afford the title compound.

Provenance & Evidence