(5-(Benzyloxy)-4-(2-((tert-butoxycarbonyl)amino)ethoxy)pyridin-2-yl)methyl acetate → (4-(2-((Tert-butoxycarbonyl)amino)ethoxy)-5-hydroxypyridin-2-yl)methyl acetate

HRID 385571Notes

Reaction equation

HRID 385571 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:23]CC2C=CC=CC=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([OH:23])=[CH:8][N:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 57815373(5-(Benzyloxy)-4-(2-((tert-butoxycarbonyl)amino)ethoxy)pyridin-2-yl)methyl acetate

Product 1

HCID 57815508(4-(2-((Tert-butoxycarbonyl)amino)ethoxy)-5-hydroxypyridin-2-yl)methyl acetateYield 70.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.8 g of (5-(benzyloxy)-4-(2-((tert-butoxycarbonyl)amino)ethoxy)pyridin-2-yl)methyl acetate in 91 mL of ethanol, 1.1 g of 10% palladium carbon was added, and the mixture was stirred at room temperature for 5 hours under a hydrogen atmosphere. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. Thereto were added chloroform and diethyl ether, and the solid was filtered off to obtain 2.1 g of (4-(2-((tert-butoxycarbonyl)amino)ethoxy)-5-hydroxypyridin-2-yl)methyl acetate as a light brown solid.

Workup

  1. filtrationThe insoluble substance was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThereto were added chloroform and diethyl ether
  4. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-91ab084c0efb4c5cbb8ab031418a633e
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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