Pyridine → N-benzyl-2-acetamido-3-methoxypropionamide

HRID 965204Notes

Reaction equation

HRID 965204 reaction equation
[CH2:1]([NH:8][C:9](=[O:15])[CH:10]([NH2:14])[CH2:11][O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C1COCC1>[CH2:1]([NH:8][C:9](=[O:15])[CH:10]([NH:14][C:22](=[O:24])[CH3:23])[CH2:11][O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 98371812-amino-N-benzyl-3-methoxypropanamide

Product 1

HCID 21634109N-benzyl-2-acetamido-3-methoxypropionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 13 (0.20 g, 0.98 mmol) in dry THF (2.0 mL) is added pyridine (0.086 g, 1.08 mmol), and then acetic anhydride (0.2 g, 1.96 mmol) is added dropwise. The reaction is stirred at room temperature for 18 hours. The solvent is evaporated in vacuo and the residue purified by flash column chromatography to obtain the above compound as the R isomer.

Workup

  1. customThe solvent is evaporated in vacuo
  2. customthe residue purified by flash column chromatography
  3. customto obtain the above compound as the R isomer

Sources & evidence

ORD record
ord-624b2097d78f48c3ab0f237a590a3d60
Source dataset
uspto-grants-1998_06
Patent number
US05773475

Reaction notes

Loading…