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

HRID 1044049

Reaktionsgleichung

Reaktionsgleichung von HRID 1044049
[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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 2826470(Benzylamino)Phenylacetic AcidAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 ml) and 1N NaOH (10 ml) was stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent was removed under reduced pressure, and the crude product was partitioned between EtOAc and water. The aqueous phase was acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase was 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.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was partitioned between EtOAc and water
  3. extractionextracted with EtOAc (three times)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9969b9ea5ecc44d4aa611407cbd7ae13
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563577B2

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