4-(S)-cyclohexyl-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyric acid tert-butyl ester → 4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-cyclohexyl-butyric acid tert-butyl ester

HRID 491902Notes

Reaction equation

HRID 491902 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][CH2:8][C@@H:9]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[NH:10][CH2:11][C:12]1[C:17]([N+:18]([O-])=O)=[CH:16][N:15]=[C:14]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:34])[CH2:7][CH2:8][C@H:9]([NH:10][CH2:11][C:12]1[C:17]([NH2:18])=[CH:16][N:15]=[C:14]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=1)[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 670236524-(S)-cyclohexyl-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyric acid tert-butyl ester

Product 1

HCID 670236004-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-cyclohexyl-butyric acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(S)-cyclohexyl-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyric acid tert-butyl ester (4.8 g, 10.2 mmol) in MeOH (50 mL) was added 10% Pd on activated carbon (0.8 g) under N2. The resulting mixture was subjected to hydrogenation at 5 psi for 2 hours. The catalyst was removed by filtration, and the MeOH was evaporated in vacuo to yield 4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-cyclohexyl-butyric acid tert-butyl ester as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe MeOH was evaporated in vacuo

Sources & evidence

ORD record
ord-9c5cb8c9a8624cd99d3322079a3612fd
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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