Hydrochloric Acid → N-(2-Fluorobenzoyl)methionine

HRID 1726374Notes

Reaction equation

HRID 1726374 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[OH-].[Na+].[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].Cl>CC(C)=O.O>[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([NH:1][CH:2]([CH2:3][CH2:4][S:5][CH3:6])[C:7]([OH:9])=[O:8])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 876(+-)-MethionineHCID 98082-Fluorobenzoyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 16771119N-(2-Fluorobenzoyl)methionine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a clear solution of D,L-methionine (10 g, 67.02 mmol) and NaOH (4.0 g, 100.53 mmol) in acetone (100 ml)/ H2O (100 ml) was added 2-fluorobenzoyl chloride dropwise with stirring between each addition. Basicity was maintained by adding 2N NaOH when necessary. After addition was completed, the reaction mixture was acidified to pH 2 with 6N HCl and extracted into EtOAc. The organic layer was dried with Na2SO4, filtered, and concentrated to give provide 2-(2-fluorobenzoylamino)-4-methylsulfanyl-butyric acid (intermediate XIIa, 13.6 g) as an oil.

Workup

  1. temperatureBasicity was maintained
  2. additionAfter addition
  3. extractionextracted into EtOAc
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give

Sources & evidence

ORD record
ord-ea2cfb8c56f442f0acdb29bc8130b6e4
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

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