Acetic Acid → HCID 131719613, compound

HRID 864871Notes

Reaction equation

HRID 864871 reaction equation
C(OC([NH:11][C@@H:12]([CH2:20][CH2:21][CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)[CH2:26][CH2:25]1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)C1C=CC=CC=1.[C:36]([OH:39])(=[O:38])[CH3:37].[H][H]>CO.[Pd]>[C:13]([OH:15])(=[O:14])[CH3:12].[C:36]([OH:39])(=[O:38])[CH3:37].[C:13]([OH:15])(=[O:14])[CH3:12].[NH2:11][C@@H:12]([CH2:20][CH2:21][CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)[CH2:26][CH2:25]1)[C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 86749926HCID 86749926, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131719613HCID 131719613, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product of step (iii) (1.34 g) and acetic acid (0.48 ml) in methanol under argon was added 10% Pd on C (100 mg). The mixture was covered with a blanket of hydrogen and stirred at room temperature for 4 hr. The catalyst was then removed by filtration through a pad of kieselguhr and the pH of the filtrate was adjusted to 4 by addition of acetic acid. To this mixture, under argon, was then added a further quantity of 10% Pd on C (100 mg)., it was covered again with hydrogen and stirred at room temperature for 3 days. The catalyst was filtered off through a pad of kieselguhr and the filtrate was evaporated to dryness. Toluene (100 ml) was then added to the residue and the solvents were again removed in vacuo to give tert. butyl (S)-2-amino-5-[1-(4-pyridyl)piperidin-4-yl]aminopentanoate, triacetate salt (1.68 g) as a yellow gum: NMR (d6 -DMSO+CD3CO2D) δ1.49 (9H, s), 1.70 (6H, m), 2.23 (2H, m), 3.03 (2H, m), 3.25 (2H, m), 3.50 (1H, m), 3.96 (1H, m), 4.30 (2H, m), 7.18 (2H, d), 8.20 (2H, d); m/Z 349 (M+H)+.

Workup

  1. customThe catalyst was then removed by filtration through a pad of kieselguhr
  2. additionthe pH of the filtrate was adjusted to 4 by addition of acetic acid
  3. additionTo this mixture, under argon, was then added a further quantity of 10% Pd on C (100 mg)
  4. stirringstirred at room temperature for 3 days
  5. filtrationThe catalyst was filtered off through a pad of kieselguhr
  6. customthe filtrate was evaporated to dryness
  7. additionToluene (100 ml) was then added to the residue
  8. customthe solvents were again removed in vacuo

Sources & evidence

ORD record
ord-d9fce7ed5d4d49ea8a4a3779b5fe040d
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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