反应详情

温度

75 °C

To N-acetonyl-8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxamide (136 mg, 0.26 mmol) in THF (3 mL) was added Burgess' Salt (155 mg, 0.65 mmol) and the reaction mixture was heated at 75° C. in a sealed vial for 2 hours. The solvents were removed under reduced pressure, and the residue was dissolved in DMF (1 mL), filtered and purified by Waters preparative LC/MS (1-99% ACN/H2O (5 mM HCl)). The desired fractions were concentrated in vacuo and the residue partitioned between EtOAc/saturated aqueous NaHCO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to yield 8-benzyl-10-(5-methyloxazol-2-yl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (76 mg, 58%) as a foam. ESI-MS m/z calc. 503.6. found 504.5 (M+1)+; Retention time: 1.74 minutes (3 min run).

1. customThe solvents were removed under reduced pressure
2. dissolutionthe residue was dissolved in DMF (1 mL)
3. filtrationfiltered
4. custompurified by Waters preparative LC/MS (1-99% ACN/H2O (5 mM HCl))
5. concentrationThe desired fractions were concentrated in vacuo
6. customthe residue partitioned between EtOAc/saturated aqueous NaHCO3 solution
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with EtOAc (2×)
9. dry with materialThe combined organics were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo