N-[[3,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]glycine methyl ester → HCID 59030678, compound

HRID 1430183Notes

Reaction equation

HRID 1430183 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][NH:5][C:6]([C:8]1[C:13]([O:14]CC2C=CC=CC=2)=[CH:12][C:11]([O:22]CC2C=CC=CC=2)=[CH:10][N:9]=1)=[O:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:30])[CH2:4][NH:5][C:6]([C:8]1[C:13]([OH:14])=[CH:12][C:11]([OH:22])=[CH:10][N:9]=1)=[O:7]

Participants

4

Reactant 1

HCID 59030679N-[[3,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]glycine methyl ester

Product 1

HCID 59030678HCID 59030678, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution [(3,5-bis-benzyloxy-pyridine-2-carbonyl)-amino]-acetic acid methyl ester (3.50 g, 8.62 mmol) in MeOH (100 mL) is added 10% Pd/C (0.350 g, 0.862 mmol) and the reaction mixture stirred under an atmosphere of H2 at room temperature for 16 hours. The suspension is filtered through Celite™ and the filtrate concentrated under reduced pressure. The crude material is purified over silica (MeOH:CH2Cl2 gradient 1% to 5%) to afford 1.95 g (quantitative yield) of the desired compound as an off-white solid. 1H NMR (250 MHz, MeOD) δ ppm 7.62 (1H, d, J=2.4 Hz), 6.53 (1H, d, J=2.4 Hz), 4.04 (2H, s), 3.64 (3H, s). HPLC-MS: m/z 227 [M+H]+.

Workup

  1. filtrationThe suspension is filtered through Celite™
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe crude material is purified over silica (MeOH:CH2Cl2 gradient 1% to 5%)

Sources & evidence

ORD record
ord-6632b96ee5c8496ea05dd3d3c3ec835e
Source dataset
uspto-grants-2015_01
Patent number
US08940773B2

Reaction notes

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