Réaction #531858

Équation de réaction

4-(3-adamantan-1-yl-ureido)butyric acid

3,7-dimethyl-oct-6-en-1-ol

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

→

798

Rendement 65.0%

4-(3-Adamantan-1-yl-ureido) butyric Acid 3,7-Dimethyl-oct-6-enyl Ester

Rendement 65.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagethe reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL)
2. 2
   Séchagethe organic layer was dried over Na2SO4
3. 3
   Concentrationconcentrated
4. 4
   AutreThe residue was purified by column chromatography on silica gel eluting with hexane and ethyl acetate (3:1)

Mode opératoire

To a solution of 4-(3-adamantan-1-yl-ureido)butyric acid 822 (0.10 g, 0.36 mmol), 4-(dimethylamino)pyridine (DMAP; 44 mg, 0.36 mmol), and 3,7-dimethyl-oct-6-en-1-ol (61 mg, 0.39 mmol) in methylene chloride (20 mL) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI; 75 mg, 0.39 mmol) at room temperature. After stirring for 12 h, the reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL), and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane and ethyl acetate (3:1) to give 798 (97 mg, 65%) as a solid: 1H NMR (CDCl3) 0.91 (3H, d, J=6.9 Hz), 1.34-1.37 (2H, m), 1.56-1.60 (9H, m), 1.67-1.69 (8H, m), 1.81 (2H, quint, J=6.9 Hz), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.35 (2H, t, J=6.9 Hz), 3.16 (2H, q, J=6.9 Hz), 4.05 (1H, s), 4.11 (2H, t, J=6.9 Hz), 4.21 (1H, s), 5.09 (1H, t, J=6.9 Hz); LC-MS (ESI) m/z calcd for C25H42N2O3 [M+H]+ 419.32. found [M+H]+ 419.22; mp 49 C. Anal. Calcd for C25H42N2O3: C, 71.73; H, 10.11; N, 6.69. Found: C, 70.27; H, 9.83; N, 6.39.

Source