Water → L-Tryptophan

HRID 616259

Reaktionsgleichung

Reaktionsgleichung von HRID 616259
C([O:3][C:4](=[O:24])[C:5]([NH:21]C=O)(C(OCC)=O)[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)C.[OH-].[Na+].O>C(O)(=O)C>[NH2:21][C@H:5]([C:4]([OH:24])=[O:3])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 292164Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate

Produkt 1

HCID 6305L-TryptophanAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 40 g (0.12 mol) of the compound of Example 6 and 24.0 g (0.60 mol) of sodium hydroxide in 240 ml. of water was heated at reflux for 18 hours. 48 ml of glacial acetic acid was added to the solution and heating was continued for an additional 8 hours. The suspension was allowed to stand at 0° overnight and the white precipitate was collected, washed with icecold water and dried to yield 24.7 g (100%) of crude product. Recrystallization from 80% aqueous acetic acid afforded, after drying at 100°/0.05 mmHg, 21.2 g (86%) of white crystals, m.p. 292° (dec.) (lit. m.p. 293°) which was identical with an authentic sample.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperatureheating
  3. waitto stand at 0° overnight
  4. customthe white precipitate was collected
  5. washwashed with icecold water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3ce9a76dbd5c4327ab3b18af5d8d444a
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04073795

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