HCID 70109737, compound → HCID 70109457, compound

HRID 843743Notes

Reaction equation

HRID 843743 reaction equation
[C:1]([O:5][C:6](=[O:46])[C@@H:7]([NH:35]C(OCC1C=CC=CC=1)=O)[CH2:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][C:18](=[O:34])[CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.CO.[Pd]>[C:1]([O:5][C:6](=[O:46])[C@@H:7]([NH2:35])[CH2:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][C:18](=[O:34])[CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:12]1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 70109737HCID 70109737, compound

Product 1

HCID 70109457HCID 70109457, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The solution of 4-(3-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionylamino}-1-piperidyl]-4-oxo-2(S)benzyloxycarbonylaminobutyric acid tert-butyl ester (1.35 g) in tetrahydrofuran (10 ml) and methanol (10 ml) was added 10% Pd—C (0.27 g, 50% wet) was hydrogenated at atmospheric pressure for 6 hours. After the catalyst was removed by filtration, the filtrate was concentrated in vacuo to give 4-[3-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionylamino}-1-piperidyl]-4-oxo-2(S)-aminobutyric acid tert-butyl ester (1.07 g) as an oil.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bb88a8b3603545dfbca5322983995296
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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