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

HRID 1393191

Reaction equation

HRID 1393191 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 with ethyl acetate and water (15 ml respectively), 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, the resulting residue was purified by silica gel column chromatography to give 0.39 g (60%) of 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide as an oily matter.

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred for three hours
  3. customThe solvent was evaporated under reduced pressure
  4. washwas 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 resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ac0a8079e4148f7a24118ec68df4687
Source dataset
uspto-grants-2008_03
Patent number
US07345064B2

Linked notes

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