HCID 86584072, compound → HCID 9803820, compound

HRID 1934399Notes

Reaction equation

HRID 1934399 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]([NH:29][CH2:30][C@H:31]([NH:35][C:36](=[O:38])[CH3:37])[C:32]([OH:34])=[O:33])=[O:28])[CH2:22]2)=[O:20])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>O1CCCC1.[Pd]>[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]([NH:29][CH2:30][C@H:31]([NH:35][C:36](=[O:38])[CH3:37])[C:32]([OH:34])=[O:33])=[O:28])[CH2:22]2)=[O:20])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 86584072HCID 86584072, compound

Product 1

HCID 9803820HCID 9803820, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[(R)-1-[3-(1-benzyloxycarbonyl-4-piperidyl)propanoyl]-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine (0.5 g) 1N HCl (0.94 ml) and 10% Pd—C (0.1 g) in tetrahydrofuran (5 ml) was hydrogenated at atmospheric pressure for 2 hours. After the catalyst was removed by filtration, the filtrate was concentrated in vacuo. The residue was resolved in water, and neutralized with saturated aqueous NaHCO3, desalted by using the resin of HP-20 eluting with isopropanol:H2O=(1:1), then freeze-dried to give N-[(R)-1-[3-(4-piperidyl)propanoyl]-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine (0.34 g, 91.0%).

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. washeluting with isopropanol
  4. dry with materialH2O=(1:1), then freeze-dried

Sources & evidence

ORD record
ord-4b86d8403b464225836b44fb29469951
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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