Methanol → 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl) ethyl]-N-pentylamide

HRID 18415

Reaktionsgleichung

Reaktionsgleichung von HRID 18415
Cl.[C:2]12([CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:20](Cl)(=[O:27])[CH2:21][O:22][CH2:23][C:24](Cl)=[O:25].C(N(CC)CC)C.[CH3:36][OH:37]>ClCCl>[C:2]12([CH2:12][CH2:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:20](=[O:27])[CH2:21][O:22][CH2:23][C:24]([O:37][CH3:36])=[O:25])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 88769Oxydiacetyl dichlorideHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

Produkt 1

HCID 574812732-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl) ethyl]-N-pentylamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(1-Adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1, 0.50 g, 1.7 mmol) was added to a solution of diglycolyl chloride (0.31 ml, 2.6 mmol) and triethylamine (0.70 ml, 5.1 mmol) in anhydrous dichloromethane (6 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. Methanol (5 ml) was added to the reaction mixture, and the whole was stirred for three hours. The solvent was evaporated under reduced pressure, the residue was distributed between ethyl acetate (15 ml) and water (15 ml), and the organic layer was washed with a saturated aqueous sodium chloride solution (5 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl)ethyl]-1-pentylamide (0.39 g, 60%) as an oily matter.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe whole was stirred for three hours
  3. customThe solvent was evaporated under reduced pressure
  4. washthe organic layer was washed with a saturated aqueous sodium chloride solution (5 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fb8549f412814648ab7a6e6616864d3a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741346B2

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