4-Methylmorpholine → Tert-butyl (2S,3S)-1-(3-hydroxyazetidin-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate

Participants

Reaction Steps

NMM (6.12 mL, 55.6 mmol) in DMF (5 mL) was added to (2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoic acid (4.15 g, 17.9 mmol), which is commercially available, in DCM (45 mL) under a nitrogen atmosphere. TBTU was added portionwise and the resultant mixture was stirred at rt for 15 min. Azetidin-3-ol hydrochloride (2.359 g, 21.53 mmol) was added and the stirring continued for 20 h. The mixture was diluted with DCM, washed with NaHCO3 and brine, filtered through a phase separator and concentrated under reduced pressure. The residue was dissolved in Et2O, washed with water, filtered through a phase separator and concentrated under reduced pressure to give the title compound (5 g, 97%). The obtained crude product was used without further purification. 1H NMR (600 MHz, CDCl3) δ 0.81-0.95, 1.04-1.16, 1.35-1.48, 1.48-1.70, 3.79-4.09, 4.14-4.24, 4.25-4.42, 4.52-4.74, 5.05-5.16.

Provenance & Evidence