Acetyl chloride → HCID 86607898, compound

Participants

Reaction Conditions

Reaction Steps

(3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (323 mg, 0.597 mmol) was dissolved in CH2Cl2 (5 mL). The solution was cooled to 0° C., then triethylamine (100 μL) and acetylchloride (50 μL) were added. The reaction was stirred for 1 h, then diluted with ethyl acetate and washed with saturated aqueous Na2CO3 (2×) and brine (2×). The organic layer was isolated, dried over Na2SO4, concentrated, and then purified via column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give (3S,4R)-1-acetyl-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (341 mg, 0.585 mmol, quant) as a colorless solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.09 (s, 3H) 1.22-1.28 (m, 9H) 1.55 (qd, J=12.93, 4.67 Hz, 1H) 1.88 (ddd, J=13.52, 2.78, 2.65 Hz, 1H) 2.07-2.10 (m, 3H) 2.33-2.39 (m, 1H) 2.75 (s, 3H) 3.09-3.18 (m, 1H) 3.24 (ddd, J=12.19, 8.53, 3.79 Hz, 1H) 3.78 (dt, J=13.58, 2.18 Hz, 1H) 4.76 (dd, J=14.91, 2.53 Hz, 1H) 5.55 (s, 2H) 7.08-7.14 (m, 2H) 7.42 (s, 1H) 7.53-7.58 (m, 1H) 7.70-7.75 (m, 1H) 7.83-7.87 (m, 2H) 7.89-7.93 (m, 1H) 8.07-8.11 (m, 1H) 9.93 (s, 1H).

Provenance & Evidence