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

HRID 274788Notes

Reaction equation

HRID 274788 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-db3bc268e03944a58d48e190eb20d693
Source dataset
uspto-grants-1995_02
Patent number
US05389680

Reaction notes

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