Benzyl Alcohol → HCID 13739162, compound

Participants

Reaction Steps

As per scheme-12, ethyl-2-bromobutyrate (12-a) is reacted with benzyl alcohol in presence of potassium hydroxide in DMF at 25° C. to 35° C. up to 3 hr to provide ethyl-2-benzyloxybutyrate (12-b). Compound 12-b is treated with hydrazine hydrate in ethanol at reflux temperature to provide corresponding acid hydrazide compound 12-c. The compound 12-c is treated with 2-picolinic acid in the presence of dehydrating agent EDC along with HOBt and N-methyl morpholine in DMF at a temperature 0° C. to 30° C. for 1 hr to provide uncyclized compound 12-d. The compound 12-d is further treated with Lawesson's reagent in tetrahydrofuran at a reflux temperature for 4 hr to provide corresponding pyridinyl-1,3,4-thiadiazolyl compound 12-e. The compound 12-e is stirred with borontribromide in dichloromethane at a temperature ranging from 0° C. to 5° C. for 1 hr followed by at 35° C. for overnight, to provide corresponding pyridinyl-1,3,4-thadiazolyl propanol compound 12-f. The compound 12-f is treated with p-nitrophenylsulfonyl chloride in the presence triethylamine in a dichloromethane at a temperature ranging from 0° C. to 15° C. to provide corresponding p-nitrophenyl sulfonic acid ester compound 12-g.

Provenance & Evidence