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Perchloric Acid → Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate

HRID 591018
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HRID 591018 반응식
[Br:1][C:2]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[S:4][C:3]=1[CH:15]([OH:20])[C:16]([O:18][CH3:19])=[O:17])[N:11]=[CH:10][CH:9]=[CH:8]3.Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(OC(=O)C)(C)(C)C>[Br:1][C:2]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[S:4][C:3]=1[CH:15]([O:20][C:6]([CH3:7])([CH3:2])[CH3:5])[C:16]([O:18][CH3:19])=[O:17])[N:11]=[CH:10][CH:9]=[CH:8]3
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참가 물질

5

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HCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 86717835Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-hydroxyacetate

생성물 1

HCID 86717834Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate수율 60.5%

시약·촉매·용매 1

HCID 10908tert-Butyl acetate용매

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온도
-5 °C

실험 절차

To a suspension of methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-hydroxyacetate (16h) (152 mg, 0.43 mmol) in tert-butylacetate (2.3 mL) at −10° C. was added perchloric acid (69.4 μL). The mixture was stirred at −5° C. for 5 hours and then warmed at room temperature for 1 hour more. The mixture was then basified with a saturated aqueous solution of sodium bicarbonate until pH 8. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by 2 preparative TLC (cyclohexane/ethyl acetate 60/40) to afford the desired product (16i) (55 mg, 0.13 mmol, 31%) as beige powder.

후처리

  1. temperaturewarmed at room temperature for 1 hour more
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by 2 preparative TLC (cyclohexane/ethyl acetate 60/40)

출처 및 근거

ORD 기록
ord-28555d43918f4061aaf848a17db85192
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238026B2

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