Pyridine → HCID 18948417, compound

HRID 1768586Notes

Reaction equation

HRID 1768586 reaction equation
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].Cl.[O:15]1[C:19]([CH2:20][CH:21]([C:23]([OH:25])=[O:24])[NH2:22])=[CH:18][CH:17]=[N:16]1>CO>[C:7]([NH:22][CH:21]([C:23]([OH:25])=[O:24])[CH2:20][C:19]1[O:15][N:16]=[CH:17][CH:18]=1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18948421HCID 18948421, compound

Product 1

HCID 18948417HCID 18948417, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 ml of pyridine and 20 ml of acetic anhydride were added to a solution of 12.45 g of 3-(5-isoxazolyl)-DL-alanine hydrochloride (prepared as described in Preparation 6) dissolved in 100 ml of methanol, whilst ice-cooling. The mixture was then stirred at room temperature for 8 hours, after which it was allowing to stand overnight. The mixture was then freed from the solvent by evaporation under reduced pressure. The residue was mixed with water and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure, to afford 10.39 g (82.3%) of the title compound as a brown oil.

Workup

  1. temperaturecooling
  2. waitto stand overnight
  3. customThe mixture was then freed from the solvent by evaporation under reduced pressure
  4. additionThe residue was mixed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-eb9c40fd83634d2cb1232df60d8a5083
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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