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

HRID 1855257Notes

Reaction equation

HRID 1855257 reaction equation
N1CCCCC1.C1C2C(COC([NH:24][C@@H:25]([CH2:29][CH2:30][CH2:31][CH2:32][N:33]([CH2:41][C:42]3[N:43]([CH3:47])[CH:44]=[CH:45][N:46]=3)[CH2:34][C:35]3[N:36]([CH3:40])[CH:37]=[CH:38][N:39]=3)[C:26]([OH:28])=[O:27])=O)C3C(=CC=CC=3)C=2C=CC=1>CN(C=O)C>[NH2:24][C@@H:25]([CH2:29][CH2:30][CH2:31][CH2:32][N:33]([CH2:41][C:42]1[N:43]([CH3:47])[CH:44]=[CH:45][N:46]=1)[CH2:34][C:35]1[N:36]([CH3:40])[CH:37]=[CH:38][N:39]=1)[C:26]([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12985318(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(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-(((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-5286fc1e9025413cbd1bdb24118c4db5
Source dataset
uspto-grants-2015_02
Patent number
US08962799B2

Reaction notes

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