Tetrahydrofuran → (S)-2-(2-Oxo-2H-pyridin-1-yl)-propionic acid

HRID 2065484Notes

Reaction equation

HRID 2065484 reaction equation
C([O:3][C:4](=[O:14])[C@@H:5]([N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=[O:13])[CH3:6])C.C1COCC1.[OH-].[Na+]>O>[O:13]=[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][N:7]1[C@@H:5]([CH3:6])[C:4]([OH:14])=[O:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66650045(S)-2-(2-Oxo-2H-pyrid-1-yl)-propionic acid ethyl ester

Product 1

HCID 53628857(S)-2-(2-Oxo-2H-pyridin-1-yl)-propionic acidYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of (S)-2-(2-Oxo-2H-pyrid-1-yl)-propionic acid ethyl ester (364 mg, 1.87 mmol), THF (2 ml), water (1 ml) and sodium hydroxide (90 mg, 2.24 mmol) was kept at room temperature for 1 h, then concentrated under reduced pressure. The residue was dissolved in ether and the resulting solution washed with water. The organic layer was discarded and the aqueous layer was acidified with concentrated HCl then extracted several times with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was triturated with ether to afford the title compound as a colorless solid (84 mg, 27%): [α]31D=−50° (c=0.2, CH3OH); 1H NMR (400 MHz, DMSO) δ 1.5 (3H, d), 5.1 (1H, q), 6.2 (1H, t), 6.4 (1H, d), 7.4 (1H, m), 7.6 (1H, d).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ether
  3. washthe resulting solution washed with water
  4. extractionthen extracted several times with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-92433ac00bc14c73b8f8770be62ed2fb
Source dataset
uspto-grants-2012_10
Patent number
US08288537B2

Reaction notes

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