Reaction #531858

Reaction equation

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

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

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

→

798

Yield 65.0%

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

Yield 65.0%

Solvents

methylene chloride

Conditions

Workup

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

Procedure

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