4-Methylmorpholine → 3-(t butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

HRID 11483

Reaction equation

HRID 11483 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.Cl.[C:30]12([CH2:40][CH2:41][NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[C:30]12([CH2:40][CH2:41][N:42]([CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH:36]3[CH2:35][CH:34]([CH2:33][CH:32]([CH2:38]3)[CH2:31]1)[CH2:39]2

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 516892Sodium BicarbonateHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

Product 1

HCID 574812723-(t butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamideYield 85.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

3-(t-Butoxycarbonylamino)propionic acid (1.0 g, 5.3 mmol) was dissolved in anhydrous tetrahydrofuran (15 ml), and N-methylmorpholine (0.6 ml, 5.5 mmol) was added to the solution. The mixture was stirred at −15° C., and isobutyl chlorocarbonate (0.7 ml, 5.4 mmol) was added thereto. Then, a solution of a free base of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (1.5 g, 5.3 mmol) in anhydrous tetrahydrofuran (15 ml) was added thereto at −18° C. The whole was stirred at 0° C. for 1.5 hours, ethyl acetate (100 ml) and a saturated aqueous sodium hydrogencarbonate solution (100 ml) were added to the reaction mixture, and the reaction mixture was distributed. The organic layer was washed with a 10% aqueous citric acid solution (100 ml), water (100 ml) and a saturated aqueous sodium chloride solution (100 ml) successively and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 1.9 g (85%) of 3-(t-butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide as an oily matter.

Workup

  1. customat −18° C
  2. stirringThe whole was stirred at 0° C. for 1.5 hours
  3. washThe organic layer was washed with a 10% aqueous citric acid solution (100 ml), water (100 ml)
  4. dry with materiala saturated aqueous sodium chloride solution (100 ml) successively and dried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3a43e2cffc69433ca1bd156c67c925a2
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Linked notes

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