Reacción #1795686

Ecuación de reacción

N,N-dimethylhydroxylamine hydrochloride

3-cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-propionic acid

1,1'-carbonyldiimidazole

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title compound

Rendimiento 171.1%

N,N-Dimethyl-O-{2-cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]propionyl}-hydroxylamine

Rendimiento 171.1%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting mixture was stirred at ambient temperature for an additional 20 minutes
2. 2
   Otropartitioned between ethyl acetate (50 mL) and saturated NaHCO3 (5 mL)
3. 3
   LavadoThe organic layer was washed with water and brine
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroPurification on a silica gel column
7. 7
   Lavadoeluting with 2:1 CH2Cl2 -EtOAc

Procedimiento

To a solution of 3-cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-propionic acid (389 mg, 1 mmol) in methylene chloride (10 mL) was added 1,1'-carbonyldiimidazole (162 mg, 1 mmol). The mixture was stirred at ambient temperature for 15 minutes and then N,N-dimethylhydroxylamine hydrochloride (147 mg, 1.5 mmol) was added. The resulting mixture was stirred at ambient temperature for an additional 20 minutes and then partitioned between ethyl acetate (50 mL) and saturated NaHCO3 (5 mL). The organic layer was washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification on a silica gel column eluting with 2:1 CH2Cl2 -EtOAc afforded 370 mg (86%) of the title compound. m.p. 98°-99° C. 1H NMR (DMSO-d6, 300 MHz) δ 0.9 (m, 2H), 1.1 (m, 4H), 1.63 (m, 6H), 1.8 m (m, 1H), 2.6 (s, 6H), 3.7 (t, J=7Hz, 1H), 5.35 (s, 2H), 7.04 (d, J=9Hz, 2H), 7.23 (d, J=9Hz, 2H), 7.62 (m, 1H), 7.68 (d, J =8Hz, 1H), 7.8 (m, 1H), 8.0 (t, J=8Hz, 2H), 8.42 (d, J=8Hz, 1H). IR (CDCl3): 1750,1600 cm-1. MS (DCI/NH3) m/e 433 (M+H)+. Analysis calcd for C27H32N2O3 : C, 74.97; H, 7.46; N, 6.48. Found: C, 74.81; H, 7.47; N, 6.41.

Fuente