Reaktion #531858

Reaktionsgleichung

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

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

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

→

798

Ausbeute 65.0%

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

Ausbeute 65.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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