HCID 86695269, compound → HCID 86695267, compound

Participants

Reaction Conditions

Reaction Steps

Into a 100-mL round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was placed a solution of tert-butyl N-(1-ethyl-4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate (330 mg, 0.72 mmol, 1.00 equiv) in 10 mL of distilled tetrahydrofuran. This solution was cooled to 0° C. Then CH3MgBr-THF (1 M, 1.5 mL) was added dropwise via syringe. The resulting solution was stirred for 2 h at this temperature. The reaction was then quenched by the addition of 10 mL of NH4Cl (aq.) and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) to give 160 mg (47%) of tert-butyl N-(1-ethyl-4-[[(3R)-3-[(2R)-2-hydroxypropyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate 199.2 as a white solid and 70 mg (20%) of tert-butyl N-(1-ethyl-4-[[(3R)-3-[(2S)-2-hydroxypropyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate 199.1 as a white solid.

Provenance & Evidence