Piperidine → (S)-2-amino-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid

HRID 77607Notes

Reaction equation

HRID 77607 reaction equation
[NH:1]1CCCCC1.[CH3:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][N:14]([CH2:23][C:24]1[N:25]([CH3:29])[CH:26]=[CH:27][N:28]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]>CN(C=O)C>[NH2:1][C@@H:19]([CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:13][C:9]1[N:8]([CH3:7])[CH:12]=[CH:11][N:10]=1)[CH2:23][C:24]1[N:25]([CH3:29])[CH:26]=[CH:27][N:28]=1)[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 674296096-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid

Product 1

HCID 46218953(S)-2-amino-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperidine (0.80 mL) was added to a solution of (S)-2-4(9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid (556 mg, 1.00 mmol) in DMF (4.0 mL). The mixture was stirred at room temperature for 2 hrs. Solvent was evaporated under reduce pressure to afford a residue, which was purified by Amberchrom to afford (S)-2-amino-6-(bis((1-methyl-1H-imidazol-2-yl)methyl)amino) hexanoic acid (330 mg, 99%). 1H NMR (400 MHz, DMSO-d6) 7.94 (s, 1H), 7.04 (d, J=3=1.2 Hz, 2H), 6.74 (d, J=1.2 Hz, 2H), 3.54 (s, 4H), 3.98 (brs, 1H), 2.88 (s, 3H), 2.72 (s, 3H), 2.35 (t, J=6.8 Hz, 2H), 1.60-1.54 (m, 1H), 1.43-1.29 (m, 3H), 1.16-1.11 (m, 2H); MS (ESI), 335 (M+H)+.

Workup

  1. customSolvent was evaporated
  2. customto afford a residue, which
  3. customwas purified by Amberchrom

Sources & evidence

ORD record
ord-9901fb4772504410ad3ba92c176180ae
Source dataset
uspto-grants-2014_09
Patent number
US08840865B2

Reaction notes

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