Hydrochloric Acid → [(2,3-Difluorobenzoyl)amino]acetic acid

HRID 1621179

Reaction equation

HRID 1621179 reaction equation
[F:1][C:2]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][CH2:7][C:8]([O:10]C)=[O:9])=[O:5].[OH-].[Li+].Cl>CO.O>[F:1][C:2]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59816250Methyl [(2,3-difluorobenzoyl)amino]acetate

Product 1

HCID 59816243[(2,3-Difluorobenzoyl)amino]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl [(2,3-difluorobenzoyl)amino]acetate (0.250 g, 1.1 mmol) in methanol (7 mL) were added lithium hydroxide (0.053 g, 2.2 mmol) and water (3 mL). The reaction mixture was allowed to stir overnight. The mixture was diluted with water (20 mL) and acidified with 1N HCl (5 mL). The product was partitioned into DCM/methanol (4:1). The organic layer was dried over sodium sulfate and the solvent removed to give [(2,3-difluorobenzoyl)amino]acetic acid which was used in the next step without purification.

Workup

  1. customThe product was partitioned into DCM/methanol (4:1)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent removed

Sources & evidence

ORD record
ord-5e5e4963e62247e5bafe92166b9bd455
Source dataset
uspto-grants-2014_07
Patent number
US08772536B2

Linked notes

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