Dl-Phenylalanine → 2-[(Methoxycarbonyl)amino]-3-phenylpropanoic acid

HRID 71952

Reaktionsgleichung

Reaktionsgleichung von HRID 71952
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].C([O-])([O-])=O.[Na+].[Na+].Cl[C:20]([O:22][CH3:23])=[O:21]>[OH-].[Na+]>[CH3:23][O:22][C:20]([NH:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4])=[O:21]

Komponenten

5

Edukt 3

HCID 994Dl-PhenylalanineHCID 6586Methyl chloroformateHCID 10340Sodium Carbonate

Produkt 1

HCID 117908102-[(Methoxycarbonyl)amino]-3-phenylpropanoic acidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Amino-3-phenyl-propionic acid (1.65 g) was dissolved in 1 N NaOH (10 mL), and Na2CO3 (530 mg) was added. The mixture was cooled to 0° C. and methyl chloroformate was added slowly, and then stirred for overnight at room temperature. The mixture was washed with DCM and acidified with 3 mL of 2N HCl, and then was taken up in ether (200 mL). The organic phase was dried over sodium sulfate. Removing the solvent to give 2-Methoxycarbonylamino-3-phenyl-propionic acid (1.95 g, 87%) as an off-white solid.

Aufarbeitung

  1. washThe mixture was washed with DCM
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customRemoving the solvent

Quellen und Nachweise

ORD-Eintrag
ord-466bd89feeb24e76a037dfab60f0c0f2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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