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

HRID 18415

반응식

HRID 18415 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb8549f412814648ab7a6e6616864d3a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741346B2

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