Sodium Hydroxide → HCID 68461539, compound

HRID 2250393Notes

Reaction equation

HRID 2250393 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[N:7]=1.[OH-].[Na+]>CO.O>[C:14]([NH:13][C:8]1[N:7]=[C:6]([CH2:5][CH2:4][C:3]([OH:17])=[O:2])[CH:11]=[C:10]([CH3:12])[CH:9]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68462790HCID 68462790, compound2×

Product 1

HCID 68461539HCID 68461539, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6.15 g of 3-(6-acetylamino-4-methylpyridin-2-yl)-propionic acid methyl ester (compound C5) is dissolved in 100 ml methanol and 70 ml water. Subsequently, 30.44 ml of a 1.0 M solution of NaOH is added while stirring is continued for 18 h at r.t. 2.0 g of amberlite IR-120 [H+]is added and the suspension is stirred for 10 min to neutralize the reaction mixture. The ion exchange resin is removed by filtration and 7.1 g of the crude product is isolated as a colourless solid after evaporation of solvent. Purification by chromatography on silica gel (eluent: dichloromethane/ethanol 10:1) affords 5.32 g of the the title compound. M.p. 202° C. ESI-MS: 223.1 (MH+). TLC: Rf=0.13 (cyclohexane/ethyl acetate 1:1+1.0 vol % acetic acid).

Workup

  1. addition2.0 g of amberlite IR-120 [H+]is added
  2. stirringthe suspension is stirred for 10 min
  3. customThe ion exchange resin is removed by filtration
  4. custom7.1 g of the crude product is isolated as a colourless solid
  5. customafter evaporation of solvent
  6. customPurification by chromatography on silica gel (eluent: dichloromethane/ethanol 10:1)

Sources & evidence

ORD record
ord-58c5f28dd55a46cb9febf8b3e542c1ee
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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