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

HRID 18415

反応式

HRID 18415 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fb8549f412814648ab7a6e6616864d3a
出典データセット
uspto-grants-2010_06
特許番号
US07741346B2

関連ノート

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