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 1043385Notes

Reaction equation

HRID 1043385 reaction equation
[C:1]([O:5][C:6](=[O:61])[CH2:7][N:8]([CH2:53][C:54](=[O:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])[C:9](=[O:52])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH2:16][N:17]([CH2:26][C:27]1[N:28]([CH2:32][C:33](=[O:51])[N:34]([CH2:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH2:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:29]=[CH:30][N:31]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([CH3:4])([CH3:3])[CH3:2].[NH:62]1CCCCC1>CN(C=O)C>[NH2:62][C@@H:22]([CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:26][C:27]1[N:28]([CH2:32][C:33]([N:34]([CH2:43][C:44]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:50])[CH2:35][C:36](=[O:42])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:51])[CH:29]=[CH:30][N:31]=1)[CH2:16][C:12]1[N:11]([CH2:10][C:9](=[O:52])[N:8]([CH2:7][C:6](=[O:61])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:53][C:54](=[O:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])[CH:15]=[CH:14][N:13]=1)[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 71561648HCID 71561648, compound

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%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-4(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-502ee182f4184e8ea095a53b497e9418
Source dataset
uspto-grants-2013_10
Patent number
US08562945B2

Reaction notes

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