2-[(3,5-Bis-benzyloxy-pyridine-2-carbonyl)-amino]-2-methylpropionic acid methyl ester → 2-[(3,5-Dihydroxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

HRID 1908296Notes

Reaction equation

HRID 1908296 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]([NH:7][C:8]([C:10]1[C:15]([O:16]CC2C=CC=CC=2)=[CH:14][C:13]([O:24]CC2C=CC=CC=2)=[CH:12][N:11]=1)=[O:9])([CH3:6])[CH3:5]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:32])[C:4]([NH:7][C:8]([C:10]1[C:15]([OH:16])=[CH:14][C:13]([OH:24])=[CH:12][N:11]=1)=[O:9])([CH3:6])[CH3:5]

Participants

4

Reactant 1

HCID 595130922-[(3,5-Bis-benzyloxy-pyridine-2-carbonyl)-amino]-2-methylpropionic acid methyl ester

Product 1

HCID 595130812-[(3,5-Dihydroxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-[(3,5-bis-benzyloxy-pyridine-2-carbonyl)-amino]-2-methylpropionic acid methyl ester, 17, (0.58 g, 1.34 mmol) in MeOH (100 mL) containing 10% Pd/C (0.116 g) is stirred under an atmosphere of H2 for 22 hours. The reaction solution is filtered through Celite™ and the collected solids are washed with hot MeOH. The combined filtrate and washings are concentrated under reduced pressure to afford 0.321 g (94% yield) of the desired compound as a grey solid. 1H NMR (250 MHz, MeOD) δ ppm 7.67 (1H, d, J=2.4 Hz), 6.58 (1H, d, J=2.4 Hz), 3.69 (3H, s), 1.56 (6H, s). HPLC-MS: m/z 255 [M+H]+.

Workup

  1. filtrationThe reaction solution is filtered through Celite™
  2. washthe collected solids are washed with hot MeOH
  3. concentrationThe combined filtrate and washings are concentrated under reduced pressure

Sources & evidence

ORD record
ord-732889cf57374bb3975eb9c203770a68
Source dataset
uspto-grants-2013_12
Patent number
US08598210B2

Reaction notes

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