Methyl 2-(benzylamino)-2-phenylacetate → (Benzylamino)Phenylacetic Acid

HRID 76974

Reaction equation

HRID 76974 reaction equation
[CH2:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12]C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[OH-].[Na+]>[CH2:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 3699844Methyl 2-(benzylamino)-2-phenylacetate

Product 1

HCID 2826470(Benzylamino)Phenylacetic AcidYield 99.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 mL) and 1N NaOH (10 mL) is stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent is removed under reduced pressure and the crude is portioned between EtOAc and water. The aqueous phase is acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase is dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (940 mg, quantitative yield), which is used in the next step without any further purification.

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionextracted with EtOAc (three times)
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8fdee344e76146e087d52fc6347b218a
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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