Hydrochloric Acid → HCID 178461482, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ester (9) (1.0 equiv) in 2.5:1 THF/MeOH (0.5 M) was treated with a solution of lithium hydroxide (3.0 equiv) in water (1.6 M), and the resulting mixture was stirred at 50° C. overnight, cooled to room temperature, acidified with 1M HCl, diluted with brine and extracted with AcOEt (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The pale yellow foam obtained was dissolved in dry DMF (0.4 M) and treated with (−)-isopinocampheyl amine (12) (1.0 equiv), followed by triethylamine (1.0 equiv) and HBTU (1.0 equiv). The resulting solution was stirred at rt for 1 h, diluted with brine and AcOEt. The layers were separated and the aqueous one was washed with brine (2×), 1M HCl and brine (2×), dried (MgSO4), filtered and concentrated under reduced pressure to provide 4-(2-phenoxyphenyl)-N-((1R,2R,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)-1H-1,2,3-triazole-5-carboxamide (13) as a pale yellow foam and was used without further purification.

Provenance & Evidence