Potassium Carbonate → HCID 67191221, compound

Participants

Reaction Steps

A 100 mL round-bottom flask was charged with of (3R)-3-((S)-1-(3-chlorophenyl)-1-hydroxy-5-methoxypentyl)-N—((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propan-2-yl)piperidine-1-carboxamide (0.6557 g, 1.0 mmol, 1.0 equiv), n-Bu4NI (3.765 g, 10 mmol, 10 equiv), and CH3CN (15 mL). To the flask was added AlCl3 (1.345 g, 10 mmol, 10 equiv) at 0° C. After 4 h, the reaction mixture was quenched with 10% aq Na2CO3 (18 mL) and 1 N aq NaOH (10 mL) and extracted with CH2Cl2 (3×). The combine organic extracts were dried over Na2SO4 and the solvent was removed in vacuo. The crude product was treated with Teoc-OSu (0.534 g, 2.06 mmol), K2CO3 (4.080 g, 29.5 mmol), water (5 mL) and CH2Cl2 (50 mL) at rt for 2.5 h. The mixture was diluted with brine, extracted with CH2Cl2 and dried over Na2SO4. After the solvent was removed in vacuo, the crude product was purified by prep HPLC (Phenomenex® Luna 5μ C18(2) 100 A, 250×21.20 mm, 5 micron, 70%→90% CH3CN/H2O, 0.1% CF3COOH over 8 min and then 90% CH3CN/H2O, 0.1% CF3COOH over 10 min, flow rate 25 mL/min) to give (3R)-3-((S)-1-(3-chlorophenyl)-1,5-dihydroxypentyl)-N—((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)piperidine-1-carboxamide (0.1625 g). LC-MS (3 min) tR=2.29 min, m/z 660, 662 (MNa+), 638, 640 (MH+).

Provenance & Evidence