[(3,5-Bis-benzyloxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester → [(3,5-Dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

HRID 1908304Notes

Reaction equation

HRID 1908304 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][NH:8][C:9]([C:11]1[C:16]([O:17]CC2C=CC=CC=2)=[CH:15][C:14]([O:25]CC2C=CC=CC=2)=[CH:13][N:12]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:33])[CH2:7][NH:8][C:9]([C:11]1[C:16]([OH:17])=[CH:15][C:14]([OH:25])=[CH:13][N:12]=1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59513083[(3,5-Bis-benzyloxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

Product 1

HCID 59513079[(3,5-Dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl esterYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [(3,5-bis-benzyloxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester, 26, (3.04 g, 6.79 mmol) in EtOH (100 mL) containing 10% Pd/C (0.300 g) is stirred under an atmosphere of H2 for 22 hours. The suspension is then filtered through Celite™, concentrated under reduced pressure, and the crude product purified over silica (2.5% MeOH/CH2Cl2) to afford 1.20 g (66% yield) of the desired compound as a colorless oil. 1H NMR (250 MHz, CDCl3) δ ppm 11.90 (1H, br s), 8.94 (1H, br s), 8.20 (1H, t, J=5.6 Hz), 7.76 (1H, d, J=2.4 Hz), 6.77 (1H, d, J=2.1 Hz), 4.13 (2H, d, J=5.5 Hz), 1.53 (9H, s). HPLC-MS: m/z 269 [M+H]+.

Workup

  1. filtrationThe suspension is then filtered through Celite™
  2. concentrationconcentrated under reduced pressure
  3. customthe crude product purified over silica (2.5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c978f7eabbba4e0b905c1c0f468ed51c
Source dataset
uspto-grants-2013_12
Patent number
US08598210B2

Reaction notes

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