Sodium Hydroxide → [(3,4,4-Trifluoro-3-butenyl)amino]oxoacetic acid

HRID 54740Notes

Reaction equation

HRID 54740 reaction equation
O=[C:2]([NH:9][C:10](=[O:15])[C:11]([O:13]C)=[O:12])[CH2:3][C:4]([F:8])=[C:5]([F:7])[F:6].[OH-].[Na+]>CO.O>[F:8][C:4](=[C:5]([F:6])[F:7])[CH2:3][CH2:2][NH:9][C:10](=[O:15])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86748464Oxo[(3,4,4-trifluoro-3-butenyl)amino]oxoacetic acid, methyl ester

Product 1

HCID 15239198[(3,4,4-Trifluoro-3-butenyl)amino]oxoacetic acidYield 25.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Compound 142 (3.16 g, 0.015 mole) in methanol (25 mL) is treated with a solution of NaOH (0.8 g, 0.02 mole) in water (5 mL). The solution is stirred at room temperature for 30 min and concentrated. The residue is dissolved in water (20 mL) and extracted with dichloromethane (2×30 mL). The aqueous layer is acidified with conc. HCl and extracted with ethyl acetate. The organic layer is dried and evaporated to give 0.75 g of the title compound as a white solid, a 25% yield. m.p. 95°-100° C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in water (20 mL)
  3. extractionextracted with dichloromethane (2×30 mL)
  4. extractionextracted with ethyl acetate
  5. customThe organic layer is dried
  6. customevaporated

Sources & evidence

ORD record
ord-1e65195886854ef28b1d1bbb05279448
Source dataset
uspto-grants-1997_04
Patent number
US05623084

Reaction notes

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