Piperidine → HCID 59408656, compound

HRID 77608Notes

Reaction equation

HRID 77608 reaction equation
N1CCCCC1.C1C2C(COC(=O)[NH:23][C@H:24]([C:45]([OH:47])=[O:46])[CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:38][C:39]3[N:40]([CH3:44])[CH:41]=[CH:42][N:43]=3)[CH2:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])C3C(=CC=CC=3)C=2C=CC=1>CN(C=O)C>[NH2:23][C@@H:24]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]([CH2:30][C:31]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:37])[CH2:38][C:39]1[N:40]([CH3:44])[CH:41]=[CH:42][N:43]=1)[C:45]([OH:47])=[O:46]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59408661HCID 59408661, compound

Product 1

HCID 59408656HCID 59408656, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperidine (0.40 mL) was added to a solution of (S)-1-(9H-fluoren-9-yl)-14,14-dimethyl-10-((1-methyl-1H-imidazol-2-yl)methyl)-3,12-dioxo-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid (190 mg, 0.33 mmol) in DMF (2.0 mL). The mixture was stirred at room temperature for 2 hrs. The solvent was evaporated under reduce pressure to afford a residue, which was purified by Amberchrom to afford (S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)((1-methyl-1H-imidazol-2-yl)methyl)amino)hexanoic acid (115 mg, 100%). 1H NMR (400 MHz, DMSO) 7.27 (brs, 1H), 7.04 (s, 1H), 6.72 (s, 1H), 3.73 (s, 2H), 3.64 (s, 3H), 3.15 (s, 2H), 3.04 (dd, J=6.8, 5.2 Hz, 1H), 2.47 (t, J=7.2 Hz, 2H), 1.65-1.46 (m, 2H), 1.39 (s, 9H), 1.30-1.21 (m, 4H); MS (ESI), 355 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-7479e43b0b654f678870668c35eb9b89
Source dataset
uspto-grants-2014_09
Patent number
US08840865B2

Reaction notes

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