Bromotrimethylsilane → HCID 68752437, compound

Participants

Reaction Conditions

Reaction Steps

1-[(2S)-1-{[(Benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (Example 24, 700 mg, 0.90 mmol) was dissolved in dry dichloromethane (30 mL), then the reaction mixture was cooled to 0° C. Trimethylsilyl bromide (TMS-Br) (0.55 g, 3.61 mmol) was added and the mixture was stirred for 2 h at room temperature. A solid formed on the walls of the round bottom flask, and the solvent was decanted. The solid was washed with ethyl acetate (20 mL) then dissolved in methanol (20 mL) and water (50 mL) was added to precipitate a solid which was filtered and dried to give crude compound (380 mg). The crude compound was purified by preparative HPLC to afford 220 mg (25.9%) of 6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-1-[(2S)-4-methyl-1-(phosphonooxy)pentan-2-yl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid.

Provenance & Evidence