Piperidine → (S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid

HRID 56337Notes

Reaction equation

HRID 56337 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([C:39]([OH:41])=[O:40])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[CH2:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:17][C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:24][C:25]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:31])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)[C:39]([OH:41])=[O:40]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59408713(s)-1-(9h-Fluoren-9-yl)-14,14-dimethyl-3,12-dioxo-10-(pyridin-2-ylmethyl)-2,13-dioxa-4,10-diazapentadecane-5-carboxylic acid

Product 1

HCID 67421779(S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of PAMA-K (0.600 g, 1.047 mmol) and piperidine (1.0 mL) in DMF (5.0 mL) was stirred at room temperature for 3 hrs. Solvent was evaporated under reduced pressure to give a residue, which was purified by Amberchrom (CG-161C) eluting with MeOH/H2O to give (S)-2-amino-6-((2-tert-butoxy-2-oxoethyl)(pyridin-2-ylmethyl)amino)hexanoic acid (0.256 g, 70%). MS (ESI), 352 (M+H)+.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customto give a residue, which
  3. customwas purified by Amberchrom (CG-161C)
  4. washeluting with MeOH/H2O

Sources & evidence

ORD record
ord-6bdca58dc5264f65ac6e03fd1a1b29f4
Source dataset
uspto-grants-2016_09
Patent number
US09433594B2

Reaction notes

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