Ethyl 2-(hydroxyimino)-3-(4,6-dibromo-3-indolyl)propanoate → 4,6-Dibromotryptophan

HRID 1078426Notes

Reaction equation

HRID 1078426 reaction equation
O[N:2]=[C:3]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Br:20])=[CH:16][C:17]=2[Br:19])[NH:12][CH:11]=1)[C:4]([O:6]CC)=[O:5]>C(O)(=O)C.[Zn]>[Br:19][C:17]1[CH:16]=[C:15]([Br:20])[CH:14]=[C:13]2[C:18]=1[C:10]([CH2:9][C@@H:3]([C:4]([OH:6])=[O:5])[NH2:2])=[CH:11][NH:12]2

Participants

4

Reactant 1

HCID 73607731Ethyl 2-(hydroxyimino)-3-(4,6-dibromo-3-indolyl)propanoate

Product 1

HCID 186560664,6-Dibromotryptophan

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Dissolve ethyl 2-(hydroxyimino)-3-(4,6-dibromo-3-indolyl)propanoate (1.47 g, 3.65 mmol) in acetic acid (200 mL) and add activated zinc dust (1.25 g, 19.2 mmol). Stir at room temperature for 72 hours. Evaporate the acetic acid in vacuo and take up in ethyl acetate (200 mL). Treat with saturated sodium hydrogen carbonate (500 mL). Filter the resulting white precipitate and separate the organic phase. Wash with saturated sodium hydrogen carbonate (100 mL) and brine (100 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound.

Workup

  1. customEvaporate the acetic acid in vacuo
  2. additionTreat with saturated sodium hydrogen carbonate (500 mL)
  3. filtrationFilter the resulting white precipitate
  4. customseparate the organic phase
  5. washWash with saturated sodium hydrogen carbonate (100 mL) and brine (100 mL)
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-5c900bea25324805b2acd079a84d0c8f
Source dataset
uspto-grants-1996_08
Patent number
US05547991

Reaction notes

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