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

HRID 1855271Notes

Reaction equation

HRID 1855271 reaction equation
C1C2C(COC([NH:18][CH:19]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:54][C:55]3[N:56]([CH2:60][C:61]([N:63]([CH2:72][C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:64][C:65](=[O:71])[O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:62])[CH:57]=[CH:58][N:59]=3)[CH2:28][C:29]3[N:30]([CH2:34][C:35](=[O:53])[N:36]([CH2:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:31]=[CH:32][N:33]=3)[C:20]([OH:22])=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:18][C@@H:19]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:28][C:29]1[N:30]([CH2:34][C:35]([N:36]([CH2:37][C:38]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:44])[CH2:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:53])[CH:31]=[CH:32][N:33]=1)[CH2:54][C:55]1[N:56]([CH2:60][C:61](=[O:62])[N:63]([CH2:72][C:73](=[O:74])[O:75][C:76]([CH3:79])([CH3:78])[CH3:77])[CH2:64][C:65](=[O:71])[O:66][C:67]([CH3:69])([CH3:68])[CH3:70])[CH:57]=[CH:58][N:59]=1)[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 781127812-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-(2-(bis(2-tert-butoxy-2-oxoethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)hexanoic acid

Product 1

HCID 67144679(S)-2-amino-6-(bis((1-(2-(bis(2-tert-butoxy-2-oxoethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)hexanoic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(bis((1-(2-(bis(2-tert-butoxy-2-oxoethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)hexanoic acid (190 mg, 0.173 mmol) and piperidine (0.50 mL) in DMF (0.50 mL) was stirred at room temperature for 1 hrs. The solvent was evaporated under reduced pressure to give a crude product. The crude product was purified by Biotage SP4 with a gradient method of 5-50% methanol in DCM to give (S)-2-amino-6-(bis((1-(2-(bis(2-tert-butoxy-2-oxoethyl)amino)-2-oxoethyl)-1H-imidazol-2-yl)methyl)amino)hexanoic acid (0.120 g, 79%). 1H NMR (400 MHz, DMSO-d6) 6.92 (s, 2H), 6.76 (s, 2H), 5.01 (s, 4H), 4.32 (s, 2H), 4.31 (s, 2H), 3.92 (s, 4H), 3.44 (s, 4H), 3.01-2.99 (m, 1H), 2.30 (t, J=7.2 Hz, 2H), 1.60-1.57 (m, 2H), 1.43 (s, 18H), 1.35 (m, 18H). 1.30-1.12 (m, 4H); MS (ESI), 439.4 (M/2+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give a crude product
  3. customThe crude product was purified by Biotage SP4 with a gradient method of 5-50% methanol in DCM

Sources & evidence

ORD record
ord-4846c56126ac4df8ba5c73e4e9d9aafd
Source dataset
uspto-grants-2015_02
Patent number
US08962799B2

Reaction notes

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