Pyridine → HCID 12084697, compound

HRID 613363Notes

Reaction equation

HRID 613363 reaction equation
Cl.C([N:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][C:6]([OH:8])=[O:7])C.[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.N1C=CC=[CH:27][CH:26]=1>CC#N>[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][C:6]([O:8][CH2:26][CH3:27])=[O:7])=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 13063265HCID 13063265, compound

Product 1

HCID 12084697HCID 12084697, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl phenylglycine, hydrochloride (prepared above) in CH3CN (60 mL) were added 4-fluorobenzoyl chloride (25.4 g, 0.16 mol) and pyridine. The resulting mixture was stirred at room temperature for about 5.5 h, then was partitioned between aqueous NaHCO3 and EtOAc. The organic extract was washed successively with 10% aqueous NaOH, 3 N HCl and saturated aqueous NaCl. The solvent was removed in vacuo, and the residue was crystallized from CH2Cl2 /hexanes to afford the title compound (19 g, 63%).

Workup

  1. customwas partitioned between aqueous NaHCO3 and EtOAc
  2. extractionThe organic extract
  3. washwas washed successively with 10% aqueous NaOH, 3 N HCl and saturated aqueous NaCl
  4. customThe solvent was removed in vacuo
  5. customthe residue was crystallized from CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-482960b18a1948ef885d32e1bb592410
Source dataset
uspto-grants-1999_12
Patent number
US06008235

Reaction notes

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