Sodium Bicarbonate → 4,6-Dichlorotryptophan

HRID 375216Notes

Reaction equation

HRID 375216 reaction equation
O[N:2]=[C:3]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[NH:12][CH:11]=1)[C:4]([O:6]CC)=[O:5].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[Cl:19][C:17]1[CH:16]=[C:15]([Cl: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

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 73607732Ethyl 2-(hydroxyimino)-3-(4,6-dichloro-3-indolyl)propanoate

Product 1

HCID 98819644,6-DichlorotryptophanYield 102.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve ethyl 2-(hydroxyimino)-3-(4,6-dichloro-3-indolyl)propanoate (1.10 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 to give a white oil. Take the white oil up in ethyl acetate (200 mL) and 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 as an amber oil (1.02 g, 98%).

Workup

  1. customEvaporate the acetic acid in vacuo
  2. customto give a white oil
  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-72ad37b3cd7248a383e8137c71ff0a35
Source dataset
uspto-grants-1996_01
Patent number
US05484814

Reaction notes

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