Amantadine → 2-[N'(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide

HRID 11442

Reaction equation

HRID 11442 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]([OH:15])=O)[CH2:9][CH2:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]12([NH2:26])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:16]12([NH:26][C:13](=[O:15])[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH3:11])[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]3)[CH2:17]1)[CH2:25]2

Participants

5

Reactant 3

HCID 2130AmantadineHCID 81531DiisopropylethylamineHCID 121366292-(((Tert-butoxy)carbonyl)(propyl)amino)acetic acid

Product 1

HCID 121366302-[N'(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Next, methylene chloride (208 ml) was added to a mixture of 2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid (4.52 g, 20.8 mmol) and 1-adamantaneamine (3.46 g, 22.9 mmol), and the whole was stirred at room temperature. N,N-Diisopropylethylamine (7.25 ml, 41.6 mmol) and then O-(7-azabenzotriazol-1-yl)-N,N,N′,N-tetramethyluronium hexafluorophosphate (8.71 g, 22.9 mmol) were added thereto, and the whole was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 7.88 g (quantitatively) of 2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide as a colorless oily matter. The obtained oily matter solidified at room temperature.

Workup

  1. stirringthe whole was stirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-352b45ba8a4c4cccbe141dd427679355
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Linked notes

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