HCID 53969602, compound → HCID 18734763, compound

HRID 843717Notes

Reaction equation

HRID 843717 reaction equation
C([O:8][C:9](=[O:29])[CH2:10][C@@H:11]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:13])C1C=CC=CC=1>O1CCCC1.[Pd]>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([NH:14][C:12](=[O:13])[C@H:11]([NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:10][C:9]([OH:29])=[O:8])[CH:16]=1

Participants

4

Reactant 1

HCID 53969602HCID 53969602, compound

Product 1

HCID 18734763HCID 18734763, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(3-pyridyl)-3(R)-(tert-butoxycarbonylamino)succinamic acid benzyl ester (4.28 g) and 10% Pd—C (0.86 g, 50% wet) in tetrahydrofuran (50 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 recrystallized from diethyl ether to give N-(3-pyridyl)-3(R)-(tert-butoxycarbonylamino)succinamic acid (2.55 g).

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-cafde8d1405849738c5b6e455a669e3a
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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