Tetrahydrofuran → HCID 57936042, compound

HRID 1912485Notes

Reaction equation

HRID 1912485 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-8ce05cf0703044338e6e82fc57355a88
Source dataset
uspto-grants-2013_12
Patent number
US08609664B2

Reaction notes

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