Tetrahydrofuran → HCID 57936042, compound

HRID 1434625Notes

Reaction equation

HRID 1434625 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:16])([CH3:15])[C:10](OCC)=O)=[CH:4][CH:3]=1.[OH-:17].[Na+].C1[CH2:23][O:22]CC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([CH3:15])([CH3:16])[CH2:10][C:23]([OH:22])=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 60994470HCID 60994470, compound

Product 1

HCID 57936042HCID 57936042, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-(4-chlorophenylamino)-2-methylpropanoate (1.2 g, 4.96 mmol) in THF (5 mL) and MeOH (2 mL), was added aqueous sodium hydroxide (3.97 g, 9.93 mmol). The mixture was heated at 50° C. for 3 h, cooled to rt, concentrated, and then neutralized to pH=3. The mixture was extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated to give 3-(4-chlorophenylamino)-3-methylbutanoic acid (0.96 g, 91% yield) as a yellow oil.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6c7992dbb33e44108ea6c2c9d3d8415d
Source dataset
uspto-grants-2009_11
Patent number
US07615556B2

Reaction notes

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