Methanol → Methyl phenylglycinate, L-

HRID 525353

Reaktionsgleichung

Reaktionsgleichung von HRID 525353
S(=O)(=O)(O)O.[NH2:6][C@@H:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9].[CH3:17]O>>[NH2:6][C@@H:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([O:10][CH3:17])=[O:9]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 99291L-Phenylglycine

Produkt 1

HCID 1201451Methyl phenylglycinate, L-Ausbeute 74 %

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A catalytic amount of concentrated sulfuric acid (0.1 mL) was added to a 50 mL round bottom flask containing a solution of (S)-2-amino-2-phenylacetic acid (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (1.0 g, 6.6 mmol) in MeOH (10 mL). The resulting mixture was heated at 65° C. for 6 hours. The solvent was removed under reduced pressure, and the mixture was quenched with aqueous NaHCO3 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to afford (S)-methyl 2-amino-2-phenylacetate (0.8 g, 74.0%) as a white solid. 1H NMR (300 MHz, CDCl3) δ: 7.37-7.32 (m, 5H), 4.62 (s, 1H), 3.70 (s, 3H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe mixture was quenched with aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e1bad738b63341ebac6fef4a45569663
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340549B2

Verknüpfte Notizen

Wird geladen…