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Sodium Bicarbonate → 4,6,Dichlorotryptophan ethyl ester

HRID 129844
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HRID 129844 반응식
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][CH2:7][CH3:8])=[O:5].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[CH2:7]([O:6][C:4](=[O:5])[C@H: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)[NH2:2])[CH3:8]
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참가 물질

6

반응물 2

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

생성물 1

HCID 228576014,6,Dichlorotryptophan ethyl ester수율 98%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 8857
Ethyl Acetate
용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c0cf8d2406ff46008d9606c47023eb33
출처 데이터셋
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05470870

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