D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)- → 4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid

HRID 1829942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829942
[NH4+].[OH:2][C:3]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([C:11]([O-:13])=[O:12])[CH2:4][C:5](=[N:9]O)[C:6]([O-:8])=[O:7].[NH4+].[H][H].O[C@@](CC1C2C(=CC=CC=2)NC=1)(C(O)=O)C[C@@H](N)C(O)=O.O[C@](CC1C2C(=CC=CC=2)NC=1)(C(O)=O)C[C@@H](N)C(O)=O>N.[C].[Rh]>[OH:2][C:3]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([C:11]([OH:13])=[O:12])[CH2:4][CH:5]([NH2:9])[C:6]([OH:8])=[O:7]

Komponenten

7

Edukt 4

HCID 9814579D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-HCID 9922096D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-HCID 178418361HCID 178418361, VerbindungHCID 1785254994-Hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutarate ammonium salt

Produkt 1

HCID 99260664-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178503043HCID 178503043, VerbindungKatalysatorHCID 222AmmoniaLösungsmittel

Versuchsvorschrift

0.13 g (0.38 mmol) of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid ammonium salt was dissolved in 5 ml of aqueous 28% ammonia, to which 0.09 g of 5% rhodium carbon was added, for reaction at ambient temperature and a hydrogen pressure of 7.5 atmospheres. 14 hours later, the catalyst was filtered off, and the resulting solution was concentrated to dryness, to obtain a mixture of 0.075 g (0.23 mmol) of the ammonium salt of (2S, 4S)/(2R, 4R)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (monatin) and 0.036 g (0.11 mmol) of the ammonium salt of (2S, 4R)/(2R, 4S)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (monatin).

Aufarbeitung

  1. additionwas added, for reaction at ambient temperature
  2. filtration14 hours later, the catalyst was filtered off
  3. concentrationthe resulting solution was concentrated to dryness
  4. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-d2b7dd0891644366b1d31fe2bb11d7e1
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064219B2

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