N2,3-bis(benzyloxy)-N5-(4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide → N5-(4-fluorobenzyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide

HRID 402558Notes

Reaction equation

HRID 402558 reaction equation
C([O:8][NH:9][C:10]([C:12]1[C:17]([O:18]CC2C=CC=CC=2)=[C:16]([CH2:26][OH:27])[C:15]([C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)=[O:29])=[CH:14][N:13]=1)=[O:11])C1C=CC=CC=1>[Pd].CO>[F:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][NH:30][C:28]([C:15]2[C:16]([CH2:26][OH:27])=[C:17]([OH:18])[C:12]([C:10]([NH:9][OH:8])=[O:11])=[N:13][CH:14]=2)=[O:29])=[CH:37][CH:36]=1

Participants

4

Reactant 1

HCID 44540937N2,3-bis(benzyloxy)-N5-(4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide2×

Product 1

HCID 44512440N5-(4-fluorobenzyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of example 1, N2,3-bis(benzyloxy)-N5-(4-fluorobenzyl)-4-(hydroxymethyl)pyridine-2,5-dicarboxamide, (0.170 g, 0.330 mmol, 1 eq) and 10% Pd/C catalyst (5 mg) were stirred in 4.0 mL of methanol under an atmosphere of hydrogen for 1 hour. The catalyst was filtered and the reaction mixture was concentrated under vacuum yielding 0.100 g of N5-(4-fluorobenzyl)-N2,3-dihydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxamide (90% yield) as a white solid; 1H-NMR (400 MHz, MeOD): δ=8.17 (s, 1H), 7.44 (m, 2H), 7.09 (t, 2H), 4.78 (s, 2H), 4.58 (s, 2H); MS-ESI m/z 336 [MH]+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-97eb5e027ceb41028fff5f78a5078e92
Source dataset
uspto-grants-2014_06
Patent number
US08742123B2

Reaction notes

Loading…