Acetic Acid → (6S,8R)-allyl-(8-azido-8-methyl-4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl)-carbamic Acid Benzyl Ester

온도

-78 °C

To a solution of the methyl diastereomers (18c) (3.90 g, 8.51 mmol) in 40 mL THF at −78° C., was added LiHMDS (IM in THF, 17.9 mL, 17.9 mmol). The red solution was stirred at −78° C. for 5 min, then a solution of trisyl azide (2.90 g, 9.36 mmol) in 8 mL THF was added. The reaction was stirred at −78° C. for 1.5 h, then was quenched with the addition of AcOH (2.19 mL, 38.3 mmol). The mixture was stirred at rt for 1 h, then was diluted with EtOAc. The organic phase was washed with 1N HCl, H2O and brine, dried (Na2SO4), and concentrated. The product was purified by flash chromatography (35 to 40% EtOAc/hexanes) to afford 2.764 g (65%) of azide 18d. MS (ESI) 500.4 (M+H+), 522.4 (M+Na+).

1. stirringThe reaction was stirred at −78° C. for 1.5 h
2. stirringThe mixture was stirred at rt for 1 h
3. washThe organic phase was washed with 1N HCl, H2O and brine
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customThe product was purified by flash chromatography (35 to 40% EtOAc/hexanes)

ORD 기록

ord-832d2b39b7bf4896951ab0ab2b27acfd

출처 데이터셋

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07094783B2