Potassium Carbonate → 2-hydroxy-3-methoxy-N-(5-methylpyridin-2-yl)propanamide

HRID 1098071Notes

Reaction equation

HRID 1098071 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH:11]([CH2:22][O:23][CH3:24])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=1)=[O:13])(=O)C>CO>[OH:10][CH:11]([CH2:22][O:23][CH3:24])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=1)=[O:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 575045701-(Methoxymethyl)-2-[(5-methylpyridin-2-yl)amino]-2-oxoethyl acetate

Product 1

HCID 574386122-hydroxy-3-methoxy-N-(5-methylpyridin-2-yl)propanamideYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydrous potassium carbonate (50 mg, 0.36 mmol) was added to a stirred solution of 1-(methoxymethyl)-2-[(5-methylpyridin-2-yl)amino]-2-oxoethyl acetate (Step 2) (1.10 g, 4.36 mmol) in MeOH (10 mL). The reaction mixture was kept at ambient temperature for 1 h before it was concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc) to give the title compound as a colourless solid (0.81 g), 1H NMR (300 MHz, CDCl3) δ 9.39 (br s, 1H), 8.14 (d, 1H), 8.09 (d, 1H), 7.53 (dd, 1H), 4.92 (br s, 1H), 4.41 (dd, 1H), 3.75 (m, 2H), 3.42 (s, 3H), 2.30 (s, 3H).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was purified with column chromatography (silica gel, eluting with EtOAc)

Sources & evidence

ORD record
ord-5258b74a7dd047e386b3133ab89c1c90
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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