Trimethylsilyldiazomethane → HCID 59315581, compound

Participants

Reaction Conditions

Reaction Steps

In a reaction vial, Intermediate 10 (1.256 g, 4.07 mmol), Intermediate 3 (0.653 g, 4.07 mmol), and glyoxylic acid monohydrate (0.375 g, 4.07 mmol) were dissolved in acetonitrile (20 mL) and DMF (5 mL). The mixture was heated in an oil bath at 80° C. for 2 h. Solvent was removed under reduced pressure, the residue was dissolved in MeOH (5 mL), and benzene (15 mL) was added. To this solution, TMS-Diazomethane (2 M in ether) (5.09 mL, 10.19 mmol) was added dropwise at rt. The mixture was stirred for 15 min at rt, then was evaporated. The residue was purified by flash chromatography: (120 g) 50-100% EtOAc/hex. Eluted at −100% EtOAc. Fractions were combined and concentrated under reduced pressure to give Intermediate 16 (1.026 g, 2.70 mmol, 66.2% yield) as a yellow powder. MS (ESI) m/z 381.3. 1H-NMR: (Jeol ECX-400) (400 MHz, CDCl3) δ ppm 1.22 (d, J=7.15 Hz, 3H) 1.53-1.64 (m, 1H) 2.34 (d, J=3.30 Hz, 3H) 3.17-3.28 (m, 1H) 3.64-3.69 (m, 1H) 3.76 (s, 3H) 5.21 (s, 2H) 6.42 (d, J=7.15 Hz, 1H) 6.86-6.92 (m, 1H) 7.03 (d, J=6.05 Hz, 1H) 7.20 (dd, J=7.97, 3.02 Hz, 1H) 7.29 (s, 1H) 7.31-7.39 (m, 2H) 7.43 (d, J=3.30 Hz, 1H).

Provenance & Evidence