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

HRID 444676Notes

Reaction equation

HRID 444676 reaction equation
[C:1]12([NH:11][C:12](=[O:20])[NH:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:21][CH:22]([CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH2:23][CH2:24]O.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:21][CH:22]([CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH2:23][CH2:24][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][NH:13][C:12]([NH:11][C:1]12[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2)=[O:20]

Participants

6

Reactant 3

HCID 8842CitronellolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114259954-(3-Adamantan-1-yl-ureido)butyric acid

Product 1

HCID 112009314-(3-Adamantan-1-yl-ureido)butyric Acid 3,7-Dimethyl-oct-6-enyl EsterYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-fcf90927d07348668fe23b82a22956f9
Source dataset
uspto-grants-2013_07
Patent number
US08476043B2

Reaction notes

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