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

HRID 444676ノート

反応式

HRID 444676 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fcf90927d07348668fe23b82a22956f9
出典データセット
uspto-grants-2013_07
特許番号
US08476043B2

反応ノート

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