HCID 11778835, compound → Monatin

HRID 2054122Notes

Reaction equation

HRID 2054122 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]2([C:19]([OH:21])=[O:20])[O:15][N:14]=[C:13]([C:16]([OH:18])=[O:17])[CH2:12]2)=[CH:2]1>N.[Rh]>[CH:6]1[CH:5]=[C:4]2[C:3]([CH2:10][C@@:11]([OH:15])([C:19]([OH:21])=[O:20])[CH2:12][C@H:13]([NH2:14])[C:16]([OH:18])=[O:17])=[CH:2][NH:1][C:9]2=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 11778835HCID 11778835, compound

Product 1

HCID 9860847MonatinYield 92.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 222AmmoniaSolvent

Procedure

404 mg (1.40 mmols) of 5-(RS)-(3-indolylmethyl)-4,5-dihydroisoxazole-3,5-dicarboxylic acid was dissolved in 8 ml of 14% aqueous ammonia solution, 250 mg of a 5% rhodium-active carbon catalyst was added thereto, and catalytic hydrogenation was conducted under a hydrogen pressure of 1 MPa for 7 hours. The catalyst was removed by filtration, and the filtrate was freeze-dried to obtain 378 mg of monatin and a small amount of DL-alanine as a by-product.

Workup

  1. customfor 7 hours
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was freeze-dried

Sources & evidence

ORD record
ord-1ff0e8bb61454b0aa9641f9eee3c7b41
Source dataset
uspto-grants-2008_02
Patent number
US07329427B2

Reaction notes

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