HCID 86695117, compound → HCID 86695261, compound

Participants

Reaction Steps

To a solution of tert-butyl N-methyl-N-(4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (370 mg, 0.83 mmol, 1.00 equiv) in freshly distilled THF (15 mL) was added dropwise bromo(ethyl)magnesium (0.46 mL, 1.25 mmol, 1.50 equiv) at 0° C. under nitrogen. The resulting solution was stirred for 2 h at r.t and quenched by the addition of H2O. The mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10-1:5) to give 0.11 g (56%) of tert-butyl N-(4-[[(3R)-3-[(2S)-2-hydroxybutyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (195.1) as a light yellow oil and 0.16 g (81%) of tert-butyl N-(4-[[(3R)-3-[(2R)-2-hydroxybutyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (196.1) as a light yellow oil.

Provenance & Evidence