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

HRID 18385

Reaction equation

HRID 18385 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.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>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

6

Reactant 4

HCID 2130AmantadineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 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 O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (8.71 g, 22.9 mmol) were added thereto successively, and the whole was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography to give 2-[N′-(t-butoxycarbonyl)-N′-propylamino]acetic acid N-(1-adamantyl)amide (7.88 g, quantitatively) as a colorless oily matter. The obtained oily matter solidified at room temperature.

Workup

  1. stirringsuccessively, and the whole was stirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-4cf23e47c95b49a18e490900848745d3
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Linked notes

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