Ammonia → HCID 23073050, compound

HRID 1295531Notes

Reaction equation

HRID 1295531 reaction equation
[CH3:1][C:2]1([CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[O:6][N:5]=[C:4]([C:7]([O:9]CC)=[O:8])[CH2:3]1.N.[H][H]>C(O)C>[NH2:5][CH:4]([CH2:3][C:2]([OH:6])([CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH3:1])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 69119475HCID 69119475, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23073050HCID 23073050, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The aforementioned 5-(RS)-methyl-5-(3-indolylmethyl)-4,5-dihydroisoxazole-3-carboxylic acid in an amount of 540 mg was dissolved in 4 ml of ethanol, and 10 ml of 28% aqueous ammonia and 300 mg of 5% Rh—C were added thereto. Reduction performed at room temperature in an atmosphere of hydrogen at 10 atm for 12 hrs. The catalyst was removed by filtration, and after vacuum concentrating the filtrate, the product was again dissolved in water followed by freeze-drying resulting in 370 mg of 2-amino-4-hydroxy-4-(3-indolylmethyl)pentanoic acid (1.41 mmol) as light brown powder (Compound No. 5 in Table 1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationafter vacuum concentrating the filtrate
  3. dissolutionthe product was again dissolved in water
  4. customby freeze-drying

Sources & evidence

ORD record
ord-1e610cf944aa46af88ac692017fb4dff
Source dataset
uspto-grants-2007_07
Patent number
US07244462B2

Reaction notes

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