Acetic Acid → (6S)-N-Phenyl-3-[3-(trifluoromethyl)benzyl(benzyloxycarbonyl)amino]-4-oxo-8beta-azido-8-methyl-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6alpha-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of the methyl diastereomers (12c) (1.02 g, 1.78 mmol) in 10 mL THF at −78° C., was added LiHMDS (1M in THF, 3.73 mL, 3.73 mmol). The red solution was stirred at −78° C. for 10 min, then a solution of trisyl azide (606 mg, 1.96 mmol) in 2 mL THF was added. The reaction was stirred at −78° C. for 1.5 h, then was quenched with the addition of AcOH (459 μL, 8.01 mmol). The mixture was stirred at rt for 1 h, then was diluted with EtOAc. The organic phase was washed with sat. NH4Cl and brine, dried (Na2SO4), and concentrated. The product was purified by flash chromatography (30 to 35% EtOAc/hexanes) to afford 784 mg (71%) of azide (12d). 1H NMR (300 MHz, CDCl3) δ9.26 (br s, 1H), 7.82 (br s, 1H), 7.51-7.25 (m, 13H), 7.10 (t, J=7.3, 1H), 5.23 (m, 3H), 4.91-4.77 (m, 2H), 2.90 (d, J=13.9, 1H), 2.43 (dd, J=13.6, 9.2, 1H), 1.87 (s, 3H); MS (ESI) 640.4 (M+Na+), 616.4 (M−H+).

Provenance & Evidence