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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 5-(1,3-thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 490220
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HRID 490220 반응식
[Br-].[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Zn+].FC(F)(F)S(O[C:14]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][CH2:16][CH:15]=1)(=O)=O>O1CCCC1>[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:16]1[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:14][CH:15]=1
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4

반응물 2

HCID 53978067tert-Butyl 3-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylateHCID 178419763HCID 178419763, 화합물

생성물 1

HCID 57440157tert-butyl 5-(1,3-thiazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To the mixture of 2-thiazolylzinc bromide (20 mL, 10 mmol) in dry tetrahydrofuran (30 mL) at 0° C. was added the product from Example 328B (3.3 gm, 10 mmol) and tetrakis(tripehynlphosphine) palladium (0) (10% mole 1.1 g). The mixture was heated at 50° C. for 1 hour, cooled to room temperature, quenched with brine and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 25% ethyl acetate:hexanes) to obtain desired product 1.4 g (60%) as colorless oil. MS (DCI/NH3) m/e 265 (M+H)+.

후처리

  1. temperaturecooled to room temperature
  2. customquenched with brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica gel, 25% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-e24430c2f5b0478ebe16d2baf030804a
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07528134B2

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