2-Hydroxy-2-[(1H-indol-3-yl)methyl]-4-(methoxyimino)pentanedioic acid → D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-

HRID 2244790Notes

Reaction equation

HRID 2244790 reaction equation
[OH:1][C:2]([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])[CH2:3][C:4](=[N:8]OC)[C:5]([OH:7])=[O:6].[H][H]>N.[C].[Rh]>[OH:1][C@@:2]([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])[CH2:3][C@@H:4]([NH2:8])[C:5]([OH:7])=[O:6].[OH:1][C@:2]([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])[CH2:3][C@@H:4]([NH2:8])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 714413032-Hydroxy-2-[(1H-indol-3-yl)methyl]-4-(methoxyimino)pentanedioic acidHCID 178418361HCID 178418361, compound

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 178503043HCID 178503043, compoundCatalystHCID 222AmmoniaSolvent

Procedure

0.264 g (0.824 mmol) of 4-hydroxy-4-(3-indolylmethyl)-2-methoxyiminoglutaric acid was dissolved in 10 ml of aqueous 28% ammonia. 0.18 g of 5% rhodium carbon (dry product) was added and the mixture stirred at a hydrogen pressure of 7.5 atmospheres for 18 hours. The catalyst was filtered off and the solvent was distilled off under reduced pressure, to obtain the residue. The resulting residue was analyzed by NMR, and a mixture of 0.115 g (0.395 mmol; yield, 48%) of (2S,4S)/(2R,4R)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (monatin) and 0.065 g (0.223 mmol; yield, 27%) of (2S,4R)/(2R,4S)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid was found to have been generated.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain the residue
  4. additiona mixture of 0.115 g (0.395 mmol; yield, 48%) of (2S,4S)/

Sources & evidence

ORD record
ord-3af2606e43cf472ab6cc6877f6653d7b
Source dataset
uspto-grants-2010_03
Patent number
US07678925B2

Reaction notes

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