Hydrochloric Acid → methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

HRID 613795

Reaktionsgleichung

Reaktionsgleichung von HRID 613795
[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].[ClH:14].[OH-].[Na+]>O.COC(=O)[C@H](CC1C=CC=CC=1)N>[ClH:14].[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 853474(R)-Methyl 2-amino-3-phenylpropanoate

Produkt 1

HCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochlorideAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 736234L-Phenylalanine, methyl esterKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

An aqueous solution of 153.2 mmol of D-phenylalanine methyl ester and 4.6 mmol of L-phenylalanine methyl ester (D/L ratio=97.1/2.9) and 335 mmol of HCl in 400 ml of pure water was neutralized to pH 3 with a 20% NaOH aqueous solution and concentrated to a weight of 100 g by means of a rotary evaporator. The concentrate was cooled to about 2° C., and the precipitated crystals were collected by filtration by suction. There was obtained 120.7 mmol of D-phenylalanine methyl ester hydrochloride having an optical purity of 99.97% as measured by HPLC.

Aufarbeitung

  1. concentrationconcentrated to a weight of 100 g by means of a rotary evaporator
  2. filtrationthe precipitated crystals were collected by filtration by suction

Quellen und Nachweise

ORD-Eintrag
ord-a88b643517434cb992fa6cae6c5fd4a5
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008403

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