Chloroacetyl chloride → 2-chloro-N-(1-(2,6-dimethoxyphenyl)-2-hydroxyethyl)-N-(4-(trifluoromethoxy)benzyl)-acetamide

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Reaction Conditions

Reaction Steps

A cooled (−10° C.) mixture of 2-(2,6-dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)-amino)ethanol (32 mg; 0.08 mmol) and NaOH (7 mg; 0.17 mmol) in DCM (1 ml) and water (0.5 ml) was treated with 2-chloroacetyl chloride (12 mg; 0.10 mmol). The resulting mixture was further stirred at −10° C., under nitrogen, for 15 min. Water and DCM were added, and the separated aq. layer was further extracted with DCM. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 2-chloro-N-(1-(2,6-dimethoxyphenyl)-2-hydroxyethyl)-N-(4-(trifluoromethoxy)benzyl)-acetamide as a yellow oil. LC-MS (conditions E): tR=0.75 min.; [M+H]+: 447.98 g/mol.

Provenance & Evidence