HCID 178418361, compound → D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-

HRID 2244791Notes

Reaction equation

HRID 2244791 reaction equation
[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.[Ni]>[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][C@@H:5]([NH2:9])[C:6]([OH:8])=[O:7].[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][C@@H:5]([NH2:9])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 1785254994-Hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutarate ammonium salt

Product 2

HCID 9814579D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-HCID 9922096D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4R)-

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

1.0 g (2.94 mmol) of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutarate ammonium salt was dissolved in 10 ml of water, to which 1 ml of a Raney-nickel catalyst (manufactured by Kawaken Fine Chemicals Co., Ltd.; developed nickel catalyst NDHT-90) was added with a syringe, and the mixture stirred at a hydrogen pressure of 20 atmospheres for 10 hours. The catalyst was filtered off, and the resulting solution was concentrated to obtain the residue. The residue was analyzed by NMR. It was shown that 0.29 g (0.89 mmol; yield, 30%) of (2S,4S)/(2R,4R)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (monatin) and 0.29 g (0.89 mmol; yield, 30%) of (2S,4R)/(2R,4S)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid were generated.

Workup

  1. additionwas added with a syringe
  2. filtrationThe catalyst was filtered off
  3. concentrationthe resulting solution was concentrated
  4. customto obtain the residue
  5. customIt was shown that 0.29 g (0.89 mmol; yield, 30%) of (2S,4S)/

Sources & evidence

ORD record
ord-d574697b4cae47d382a45714c30a3689
Source dataset
uspto-grants-2010_03
Patent number
US07678925B2

Reaction notes

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