Ammonium formate → 2-(6-Amino-5-ethoxy-pyridin-3-yl)-2-hydroxy-propionic acid ethyl ester

HRID 1611968Notes

Reaction equation

HRID 1611968 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([C:8]1[CH:9]=[N:10][C:11]([N+:17]([O-])=O)=[C:12]([O:14][CH2:15][CH3:16])[CH:13]=1)([OH:7])[CH3:6])[CH3:2].C([O-])=O.[NH4+].C1COCC1.CO>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[C:5]([C:8]1[CH:9]=[N:10][C:11]([NH2:17])=[C:12]([O:14][CH2:15][CH3:16])[CH:13]=1)([OH:7])[CH3:6])[CH3:2]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 21899815MeOH tetrahydrofuranHCID 69546028HCID 69546028, compound

Product 1

HCID 235938112-(6-Amino-5-ethoxy-pyridin-3-yl)-2-hydroxy-propionic acid ethyl esterYield 74.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(6-nitro-5-ethoxy-pyridin-3-yl)-2-hydroxy-propionic acid ethyl ester (1.3 g), ammonium formate (1.5 g), and 10% Pd/C (100 mg) was stirred in a 1:1 mixture of THF/methanol overnight. The reaction mixture was filtered through diatomaceous earth, and the filtrate evaporated to yield an oil. The oil was dissolved in EtOAc, washed with water and brine, and the organic layer separated and dried over magnesium sulfate. Evaporation furnished 863 mg of the title compound. LC/MS+=255.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe filtrate evaporated
  3. customto yield an oil
  4. washwashed with water and brine
  5. customthe organic layer separated
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation

Sources & evidence

ORD record
ord-938dc0a2011042829e05a789f08d2078
Source dataset
uspto-grants-2006_01
Patent number
US06992092B2

Reaction notes

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