2,6-Difluorobenzoyl chloride → n-(2,6-Difluorobenzoyl)serine methyl ester

HRID 35935

Reaction equation

HRID 35935 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[CH:5]([CH2:7][OH:8])[NH2:6].[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:12]=1[C:13](Cl)=[O:14]>N1C=CC=CC=1>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][C:13](=[O:14])[C:12]1[C:11]([F:10])=[CH:19][CH:18]=[CH:17][C:16]=1[F:20]

Participants

4

Reactant 2

HCID 874382,6-Difluorobenzoyl chlorideHCID 517373Methyl DL-serinate hydrochloride

Product 1

HCID 53828973n-(2,6-Difluorobenzoyl)serine methyl esterYield 39.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 39.0 g (251 mmol.) of D,L-serine methyl ester hydrochloride and 800 ml of pyridine, there was added dropwise 37 ml (324 mmol.) of 2,6-difluorobenzoylchloride with stirring at room temperature for 5 hours. Then the reaction mixture was further stirred at the same temperature for 2 hours. After the reaction was completed, the resultant mixture was concentrated under reduced pressure. To the residue, there was added 500 ml of chloroform. The mixture was washed with water, extracted with chloroform, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 25.88 g of N-(2,6-difluorobenzoyl)serine methyl ester as a colorless oily substance (nD22.9 1.5038).

Workup

  1. stirringThen the reaction mixture was further stirred at the same temperature for 2 hours
  2. concentrationthe resultant mixture was concentrated under reduced pressure
  3. additionTo the residue, there was added 500 ml of chloroform
  4. washThe mixture was washed with water
  5. extractionextracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-624df8356d474168b5d0c6bd89d12f6b
Source dataset
uspto-grants-1995_05
Patent number
US05411979

Linked notes

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