Triethylamine → HCID 131735387, compound

Participants

Reaction Steps

To a solution of 2.6 mL (19 mmol) of triethylamine in 56 mL of anhydrous THF was added 2.47 g (19 mmol) of 4-oxo-hexanoic acid (Sigma Aldrich, Milwaukee Wis.). The reaction was stirred for 15 min at rt under a N2 atmosphere after which 2.4 mL (19 mmol) of isobutyl chloroformate was added drop wise by a syringe. The reaction was stirred for 3.0 h during which time a white precipitate formed. The 4-oxo-hexanoic acid carbonic anhydride was used in the next step without further purification. To a solution of 3.6 g (17 mmol) of mannosamine hydrochloride in 112 mL of 1:1 H2O/THF was added 3.1 mL (22 mmol) of triethylamine. The solution was stirred for 15 min at rt after which the 4-oxo-hexanoic acid carbonic anhydride was added drop wise by an addition funnel. The reaction was stirred for another 36 h under a N2 atmosphere and the solution was concentrated in vacuo. The crude compound was acetylated by treatment with 40 mL of 2:1 Pyr/Ac2O. The reaction was stirred for 12 h at rt and then the solution was concentrated in vacuo. The resulting syrup was washed with 1.0 M HCl (2×30 mL) and saturated NaHCO3 (1×30 mL), then dried over Na2SO4. Purification of the crude compound by silica gel chromatography yielded a white foam.

Provenance & Evidence