Sodium Hydroxide → 3-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl)propanoic acid

HRID 1828411Notes

Reaction equation

HRID 1828411 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22063539Methyl 3-{2-[(tert-butoxycarbonyl)amino]-4-pyridyl}propanoate

Product 1

HCID 220637293-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl)propanoic acidYield 38.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-{2-[(tert-butoxycarbonyl)amino]-4-pyridyl}propanoate (30.65 g, 0.11 mol) dissolved in methanol (200 ml) was added with 1 N aqueous sodium hydroxide (164 ml) and stirred at room temperature for 21 hours. After the solvent was evaporated under reduced pressure and the residue was washed with diethyl ether, the resulting aqueous layer was added with concentrated hydrochloric acid until pH of the layer became 1. The solution was washed with ethyl acetate, and the resulting aqueous layer was neutralized by further adding sodium hydroxide. The solution was extracted with chloroform:methanol=10:1, and the resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 11.16 g (38%) of the title compound as yellow crystals without purification.

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. washthe residue was washed with diethyl ether
  3. additionthe resulting aqueous layer was added with concentrated hydrochloric acid until pH of the layer
  4. washThe solution was washed with ethyl acetate
  5. additionby further adding sodium hydroxide
  6. extractionThe solution was extracted with chloroform
  7. dry with materialmethanol=10:1, and the resulting organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79858689e25c4bf8ad86112a4a74d511
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

Loading…