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Bromoacetic Acid → 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

HRID 11479
Notes
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Reaction equation

HRID 11479 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=O.CN1CCOCC1.C(Cl)(=O)OCC(C)C.Cl.[C:22]12([CH2:32][CH2:33][NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[C:22]12([CH2:32][CH2:33][N:34]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:3](=[O:5])[CH2:2][Br:1])[CH2:29][CH:28]3[CH2:27][CH:26]([CH2:25][CH:24]([CH2:30]3)[CH2:23]1)[CH2:31]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 6227Bromoacetic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

Product 1

HCID 574798992-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

Bromoacetic acid (0.50 g, 3.6 mmol) was dissolved in anhydrous tetrahydrofuran (20 ml), and the solution was stirred at −15° C. under a nitrogen atmosphere. N-Methylmorpholine (0.40 ml, 3.6 mmol) and isobutyl chlorocarbonate (0.45 ml, 3.5 mmol) were added to the solution. Then, a solution of a free base of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (1.0 g, 3.5 mmol) in anhydrous tetrahydrofuran (20 ml) was added dropwise to the mixture. The whole was stirred at 0° C. for 1.5 hours, a saturated aqueous sodium hydrogencarbonate solution (70 ml) and ethyl acetate (70 ml) were added to the reaction mixture, and the reaction mixture was distributed. The ethyl acetate layer was washed with water (70 ml) and a saturated aqueous sodium chloride solution (70 ml) successively and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure to give 1.3 g (quantitatively) of 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide as a oily matter.

Workup

  1. stirringThe whole was stirred at 0° C. for 1.5 hours
  2. washThe ethyl acetate layer was washed with water (70 ml)
  3. dry with materiala saturated aqueous sodium chloride solution (70 ml) successively and dried over anhydrous magnesium sulfate
  4. concentrationThe ethyl acetate layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7be440cf55a742dbbf2f5f861b28233a
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098226B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes