Sodium Carbonate → Methyl (S)-3-amino-3-phenylpropanoate

HRID 1351403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351403
[NH2:1][C@H:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][C:7](C)(C)C)=[O:5].C(=O)([O-])[O-].[Na+].[Na+]>Cl>[NH2:1][C@H:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 70210931,1-Dimethylethyl (betaS)-beta-aminobenzenepropanoate

Produkt 1

HCID 788099Methyl (S)-3-amino-3-phenylpropanoateAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (3S)-3-amino-3-phenylpropanoate (5.04 g, 22.9 mmol) in 2.25M methanolic hydrochloric acid (100 ml) was heated under reflux for 2 hours. The mixture was cooled to room temperature, basified with saturated sodium carbonate solution to pH 8 and the phases separated. The aqueous layer was extracted with dichloromethane (4×), the combined organic solutions were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to afford the title compound 3.97 g.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. customthe phases separated
  3. extractionThe aqueous layer was extracted with dichloromethane (4×)
  4. washthe combined organic solutions were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f29db50caee34cfe844b4f76a9e07357
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217714B1

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