Sodium Bicarbonate → 4,6-Dichlorotryptophan

HRID 2379115Notes

Reaction equation

HRID 2379115 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 (1.10g, 3.65mmol ) in acetic acid (200mL) and add activated zinc dust (1.25g, 19.2mmol). 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 (200mL) and treat with saturated sodium hydrogen carbonate (500mL). Filter t he resulting white precipitate and separate the organic phase. Wash with saturated sodium hydrogen carbonate (100mL) a nd brine (100mL). Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as an amber oil (1.02g, 98%).

Workup

  1. customEvaporate the acetic acid in vacuo
  2. customto give a white oil
  3. filtrationFilter t he
  4. customresulting white precipitate
  5. customseparate the organic phase
  6. washWash with saturated sodium hydrogen carbonate (100mL) a nd brine (100mL)
  7. dry with materialDry (MgSO4)
  8. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-91b2a14549d34064bd5fdeb649cd133c
Source dataset
uspto-grants-1994_11
Patent number
US05360814

Reaction notes

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