Triethylsilane → HCID 58113857, compound

Participants

Reaction Steps

3-[[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-(4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-5-trimethylsilanyloxy-pent-1-ynyl)-thiophene-2-carboxylic acid methyl ester (230 mg, 0.34 mmol) was added to a solution of tetrahydro-pyran-4-one (29 mg, 0.29 mmol) and FeCl3 (2.8 mg, 0.017 mmol) in nitromethane (5.0 mL) at 0° C. Triethylsilane (0.054 mL, 0.34 mmol) was added and the reaction warmed to room temperature and stirred for 2 h. Sat. NaHCO3 was added and the reaction extracted with dichloromethane. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to give the crude product. Purification by HPLC with CH3CN (0.1% TFA)/H2O (0.1% TFA) provided 5-[3,3-dimethyl-5-(tetrahydro-pyran-4-yloxy)-pent-1-ynyl]-3-[(4-hydroxy-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (8 mg, 4%) as solid.

Provenance & Evidence